Name: 1273-86-5|Ferrocenemethanol|97%
Brand: Ambeed
SKU: A476446
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1
[ 1273-86-5 ]
[ 12093-10-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With ferrocene-labeled Merrifield resin-supported ionic liquid ([FemDMMerA]RuO₄) In tetrahydrofuran for 4h; Reflux; Green chemistry;	General procedure for the oxidation of alcohols General procedure: A mixture of aryl alcohol (1 mmol) and [FemDMMerA]Y (100 mg) in solvent(5 mL) was refluxed in oil bath. After completion of the reaction as monitored byTLC, the reaction mixture was filtered to remove insoluble SILP catalyst.Evaporation of solvent in vacuuo followed by column chromatography over silicagel using petroleum ether/ethyl acetate (95:5 v/v) afforded pure aldehydes.
90%	With C₃₄H₃₇N₄O₆Ru₂⁽¹⁺⁾*Cl^(1-); potassium hydroxide In toluene at 70℃; for 6h; Schlenk technique; Inert atmosphere;
88%	With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; TPGS-750-M; copper(I) bromide In water at 20℃; for 24h;

78%	With oxygen; potassium carbonate In toluene at 80℃; for 24h;	Aerobic oxidation of benzyl alcohols A mixture of K2CO3 (1 mmol) and the catalyst (52 mg, ∼3 mol% of Pd2+) in toluene (5 ml) was prepared in a two necked flask. The flask was evacuated and refilled with pure oxygen. To this solution, the alcohol (1 mmol, in 1 ml toluene) was injected and the resulting mixture was stirred at 80 °C under an oxygen atmosphere. After completion of reaction, the reaction mixture was filtered off and the catalyst rinsed twice with CH2Cl2 (5 ml). The excess of solvent was removed under reduced pressure to give the corresponding carbonyl compounds.
77%	With pyridine; 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In tetrahydrofuran all mixed in THF, refluxed for 5 h; evapd.(vac.), diluted (H2O), extd.(CH2Cl2), org. layer washed (10% HCl),dried (Na2SO4), evapd., chromy.(silica gel-10% ethyl acetate in petrole um ether);
72%	With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium hydride In tetrahydrofuran; mineral oil to a suspn. of NaH in mineral oil in THF added dropwise Fe complex in THF at 0°C, warmed to room temp., stirred for 30 min, treated with ligand in THF, refluxed for 3 h; cooled to room temp., evapd.(vac.), chromy.(alumina-petroleum ether-CH2Cl2 1:1), elem. anal.;

Reference： [1]Kurane, Rajanikant; Bansode, Prakash; Khanapure, Sharanabasappa; Salunkhe, Rajashri; Rashinkar, Gajanan [Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 7807 - 7821]
[2]Dutta, Indranil; Sarbajna, Abir; Pandey, Pragati; Rahaman, S. M. Wahidur; Singh, Kuldeep; Bera, Jitendra K. [Organometallics, 2016, vol. 35, # 10, p. 1505 - 1513]
[3]Lipshutz; Hageman; Fennewald; Linstadt; Slack; Voigtritter [Chemical Communications, 2014, vol. 50, # 77, p. 11378 - 11381]
[4]Alizadeh; Khodaei; Kordestania; Beygzadeh [Journal of Molecular Catalysis A: Chemical, 2013, vol. 372, p. 167 - 174]
[5]Sengupta, Saumitra [Polyhedron, 2003, vol. 22, # 9, p. 1237 - 1240]
[6]Sengupta, Saumitra [Polyhedron, 2003, vol. 22, # 9, p. 1237 - 1240]

2
[ 16853-85-3 ]
[ 1273-86-5 ]
methyl ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With aluminium trichloride In diethyl ether in abs. ether;;
	With aluminium trichloride In diethyl ether in abs. ether;;
	In diethyl ether in abs. ether;;

With AlCl₃ In diethyl ether in abs. ether;;

Reference： [1]Benkeser,R.A.; Bach,J.L. [Journal of the American Chemical Society, 1964, vol. 86, p. 890 - 895] Schloegl, K.; Mohar, A.; Peterlik, M. [Monatshefte fur Chemie][Monatshefte fuer Chemie, 1961, vol. 92, p. 921 - 926] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.1.4.1, page 253 - 255] Bach, J. L. [Dissertation abstracts, Diss. Purdue Univ. 1963, 1964, vol. 25, p. 824] Dabard, R.; Dixneuf, P. [Bulletin de la Societe Chimique de France][Bulletin de la Societe Chimique de France, 1969, p. 2158 - 2164]
[2]Benkeser,R.A.; Bach,J.L. [Journal of the American Chemical Society, 1964, vol. 86, p. 890 - 895] Schloegl, K.; Mohar, A.; Peterlik, M. [Monatshefte fur Chemie][Monatshefte fuer Chemie, 1961, vol. 92, p. 921 - 926] Dabard, R.; Dixneuf, P. [Bulletin de la Societe Chimique de France][Bulletin de la Societe Chimique de France, 1969, p. 2158 - 2164]
[3]Sokolova, E. B.; Shebanova, M. P.; Leizerakh, V. S. [Zhurnal Obshchei Khimii, 1967, vol. 37, p. 1512 - 1514][Zhurnal Obshchei Khimii, 1967, vol. 37, p. 1594 - 1596] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.1.1, page 245 - 248]
[4][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.1.1, page 245 - 248] Schloegl, K.; Fried, M. [Monatshefte fur Chemie][Monatshefte fuer Chemie, 1964, vol. 94, p. 558 - 575]

3
[ 12093-10-6 ]
[ 1273-86-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere;
98%	With C₄₆H₄₉CoN₃P₄⁽²⁺⁾*2BF₄^(1-); hydrogen; potassium hydroxide In ethanol; acetonitrile at 60℃; for 24h; Autoclave; Glovebox; chemoselective reaction;
97%	With lithium aluminium tetrahydride at 45℃; for 2h; Inert atmosphere; Reflux;	3.2 (2) Synthesis of ferrocene methanol: ferrocene formaldehyde (10 g, 0.047 µM) dissolved in anhydrous ethyl ether in, and transfer it to the constant pressure in the dropping funnel; in three-neck round bottom flask is added in the tetrahydro (1.8 g, 0 . 047 µM), under the protection of the helium, the ferrocene formaldehyde solution is slowly dripped into stirring in in the tetrahydro solution, then completing after 45 °C reflow 2 h, for at the same time thin-layer chromatographic monitoring the reaction; after the reaction, cooling to room temperature, then adding 60 ml ethyl ether, excessive cooling of the tetrahydro adding ethyl acetate and water mixture is removed; separatory funnel for the organic layer is separated out, and washing by water three times (once for each 100 ml water); and organic water-free magnesium sulfate drying 24 h after, for after the Rotavapor distillation under reduced pressure, to obtain yellow powder 7.32 g, yield 97%, melting point 76 - 78 °C.

96%	With lithium aluminium tetrahydride In diethyl ether at 45℃; for 2h; Inert atmosphere; Schlenk technique;
89%	With sodium tetrahydroborate In tetrahydrofuran; ethanol at 0 - 20℃; for 3h;	1 Ferrocenemethanol (2a) Synthesis Ferrocene carboxyl aldehyde (0.100 g, 0.467 mmol) was dissolved in ethanol (8 mL), was added slowly in small portions sodium borohydride (0.090 g, 2.4mmol) at 0 . The reaction mixture was stirred at ambient temperature for 3 hours. It was add water (3mL) and dichloromethane (10 mL) in turn to complete the reaction.The organic layer was separated and the remaining water layer was extracted three times with dichloromethane (15mL x 3). The combined organic layer is washed with a saturated aqueous sodium chloride solution, placed into the over anhydrous sodium sulfate, filtered under reduced pressure. After removal of all the solvent in the filtrate under reduced pressure was purified by column chromatography (hexane: ethyl acetate: methanol = 15: 5: 1) to give the compound 2a to give a yellow solid. (0.090 g, 89%)
88%	With dimethylsulfide borane complex In tetrahydrofuran for 2h; Inert atmosphere; Schlenk technique; Cooling with ice;
84%	With [Ni(1,3-dimesitylimidazol-2-ylidene)Clcyclopentadienyl]; sodium triethylborohydride; diphenylsilane In tetrahydrofuran at 25℃; for 17h; Inert atmosphere; Schlenk technique;
83%	Stage #1: ferrocenecarboxaldehyde With nickel(II) acetate tetrahydrate; tricyclohexylphosphine In tetrahydrofuran at 70℃; for 16h; Stage #2: With sodium hydroxide In methanol
68%	Stage #1: ferrocenecarboxaldehyde With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); phenylsilane In toluene for 0.5h; Reflux; Stage #2: With tetrabutyl ammonium fluoride In toluene at 20℃; for 0.5h; chemoselective reaction;	4.3. General procedure for the reduction of solid aldehydes with the system PhSiH₃/[CpRu(PPh₃)₂Cl] General procedure: To a solution of [CpRu(PPh3)2Cl] (1 mol%) and solid aldehyde (1.0 mmol) in toluene (3 ml) was added PhSiH3 (1.2 mmol). The reaction mixture was stirred at reflux temperature under an air atmosphere (the reaction times are indicated in Table 4). Then, TBAF (1.0 mmol) was added and the reaction mixture was stirred at room temperature during 30 min. After evaporation, the reaction mixture was purified by silica gel column chromatography with ethyl acetate:n-hexane (1:3) to afford the corresponding alcohols.
59%	With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃;
	With borohydride
	With sodium tetrahydroborate In tetrahydrofuran
	With lithium aluminium hydride In diethyl ether reduction under Ar, Schlenk techniques;
	With lithium aluminium tetrahydride In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 0.5h; Inert atmosphere;	Synthesis of ferrocenylcarbinol derivatives 9 General procedure: To a clean and dry round bottom flask with a septum, 3-5mmol of the ferrocenylketone were added and approximately 20mL of dimethoxyethane (DME) were transferred with a positive nitrogen pressure; the mixture was stirred to obtain a reddish solution. 0.75equivalents of lithium aluminum hydride (1M in tetrahydrofuran) were added, and a change of color from red to yellow in the solution was observed. The reaction was stopped after 30min at room temperature; complete transformation was confirmed with TLC. After this time, Glauber's salt was added and the mixture was stirred until a formation of a granular precipitate was observed. The mixture was filtered, and the solvent was eliminated to obtain yellow to orange oils or solids. The compounds were employed directly for following reactions without further purification.
	With sodium tetrahydroborate In methanol Sealed tube;
	With sodium tetrahydroborate; ethanol In tetrahydrofuran for 0.5h; Inert atmosphere; Sealed tube;	1 To a round bottomed flask equipped with a magnetic stirrer bar was added ferrocene carboxaldehyde(535 mg, 2.5 mmol, 1 eq). The flask was then charged with ethanol (4 cm3) and THF (1 cm3). Thered solution was then treated with sodium borohydride (123 mg, 3.2 mmol, 1.3 eq). The flask wasthen sealed and placed under a nitrogen atmosphere. After 30 minutes the solution had changedcolour to an orange and TLC analysis indicated full consumption of the starting material. The flaskwas then concentrated to 90% of original volume in vacuo. The dark orange residue was then takenup in EtOAc (15 cm3) and NaHCO3 (15 cm3). The bi-phasic mixture was transferred to separatingfunnel, the aqueous layer was separated and then back extracted with EtOAc (3 x 5 cm3), thecombined organic washings were then dried over MgSO4, filtered and then concentrated in vacuo togive a yellow solid. The ferrocene methanol was then taken up in 1,3-propanediol (5 cm3), the yellowsolution was then treated with ytterbium (Ill) triflate (77 mg, 0.125 mmol, 5 mol%). The flask wasthen sealed and heated to 100 °C. After heating for 10 minutes TLC analysis indicated fullconsumption of the starting material. The flask was cooled to room temperature, diluted with H20(20 cm3) and EtOAc (20 cm3). The organic layer was then separated and the aqueous layer backextracted with EtOAc (3 x 5 cm3). The combined organic layers were then washed with H20 (2018 cm3) and brine (sat) (20 cm3) then dried over MgSO4, filtered then concentrated in vacuo to give an orange solid. Purification was then carried out by silica-gel chromatography eluting with n-Hex 1:1 EtOAc to give the desired product 3-(ferrocenyloxy)propan-lol (1) as an orange powder (514 mg, 74%).‘H NIVIR (250 MHz, CDC13); oH: 4.24 (s, 4H), 4.11 (s, 6H), 3.65 (t, 2H, J 5.4 Hz), 3.54 (t, 2HJ=5.4 Hz), 3.65 (t, 2H J = 5.4 Hz), 2.52 (br s, 1H), 1.7 (quin 2H, J = 5.6 Hz); ‘3C NIVIR (75 IVIHz, CDC13); Oc: 83.6, 77.3, 71.5, 69.4, 69.3, 69.2, 68.7, 32.0; HRMS (ESI iTOF) calculated for C,4H,8FeO2Na m/z 297.0553 found 297.0560 (m/z + Na); Electrochemical potential: 181 mV.
	With sodium tetrahydroborate
	With sodium tetrahydroborate In tetrahydrofuran; methanol
	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; C₁₉H₂₃N₂O₈PS^(2-)*2Na⁽¹⁺⁾; sodium formate; alkaline phosphatase In ethanol at 37℃; for 0.5h;
	With sodium tetrahydroborate In methanol
	With sodium tetrahydroborate In methanol Inert atmosphere; Schlenk technique;
	With sodium tetrahydroborate In isopropyl alcohol
	With sodium tetrahydroborate In tetrahydrofuran
	With sodium tetrahydroborate In ethanol
	With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 2h;
	With sodium tetrahydroborate
	With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 24h; Inert atmosphere; Schlenk technique;
	With methanol; sodium tetrahydroborate at 0 - 20℃; Schlenk technique; Inert atmosphere;

Reference： [1]Hooper, Joel F.; Seo, Sangwon; Truscott, Fiona R.; Neuhaus, James D.; Willis, Michael C. [Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1630 - 1634]
[2]Duan, Ya-Nan; Du, Xiaoyong; Cui, Zhikai; Zeng, Yiqun; Liu, Yufeng; Yang, Tilong; Wen, Jialin; Zhang, Xumu [Journal of the American Chemical Society, 2019, vol. 141, # 51, p. 20424 - 20433]
[3]Current Patent Assignee: SHANDONG YUANGEN PETROLEUM CHEMICAL - CN104710482, 2018, B Location in patent: Paragraph 0033; 0038; 0043
[4]Ikhile, Monisola I.; Bala, Muhammad D.; Nyamori, Vincent O.; Ngila, J. Catherine [Applied Organometallic Chemistry, 2013, vol. 27, # 2, p. 98 - 108]
[5]Current Patent Assignee: DIATECH KOREA CO LTD; SOGANG UNIVERSITY - KR101583811, 2016, B1 Location in patent: Paragraph 0052; 0054; 0061; 0062
[6]Horký, Filip; Císařová, Ivana; Štěpnička, Petr [Chemistry - A European Journal, 2021, vol. 27, # 4, p. 1282 - 1285]
[7]Bheeter, Linus P.; Henrion, Mickael; Brelot, Lydia; Darcel, Christophe; Chetcuti, Michael J.; Sortais, Jean-Baptiste; Ritleng, Vincent [Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2619 - 2624]
[8]Zheng, Jianxia; Darcel, Christophe; Sortais, Jean-Baptiste [Catalysis science and technology, 2013, vol. 3, # 1, p. 81 - 84]
[9]Cabrita, Ivânia R.; Florindo, Pedro R.; Fernandes, Ana C. [Tetrahedron, 2017, vol. 73, # 11, p. 1511 - 1516]
[10]Gharib, Bhasem; Hirsch, Andreas [European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4123 - 4136]
[11]Allen, Christopher W.; Myer, Charles N. [Phosphorus, Sulfur and Silicon and the Related Elements, 1997, vol. 124, p. 431 - 435]
[12]Floris, Barbara; Galloni, Pierluca; Seraglia, Roberta; Tagliatesta, Pietro [Journal of Organometallic Chemistry, 2003, vol. 679, # 2, p. 202 - 207]
[13]Nxumalo, Edward N.; Chabalala, Vongani P.; Nyamori, Vincent O.; Witcomb, Michael J.; Coville, Neil J. [Journal of Organometallic Chemistry, 2010, vol. 695, # 10-11, p. 1451 - 1457]
[14]García-Barrantes, Pedro M.; Lamoureux, Guy V.; Pérez, Alice L.; García-Sánchez, Rory N.; Martínez, Antonio R.; San Feliciano, Arturo [European Journal of Medicinal Chemistry, 2013, vol. 70, p. 548 - 557]
[15]Nikolaienko, Pavlo; Pluta, Roman; Rueping, Magnus [Chemistry - A European Journal, 2014, vol. 20, # 32, p. 9867 - 9870]
[16]Current Patent Assignee: BINX HEALTH LIMITED - WO2015/52516, 2015, A1 Location in patent: Page/Page column 18
[17]Kumar, Dhananjay; Singh, Anoop S.; Tiwari, Vinod K. [RSC Advances, 2015, vol. 5, # 40, p. 31584 - 31593]
[18]Watanabe, Motonori; Chang, Yuan Jay; Chou, Po-Ting; Staykov, Aleksandar; Shibahara, Masahiko; Sako, Katsuya; Ishihara, Tatsumi; Chow, Tahsin J. [Tetrahedron Letters, 2015, vol. 56, # 12, p. 1548 - 1551]
[19]Goggins, Sean; Marsh, Barrie J.; Lubben, Anneke T.; Frost, Christopher G. [Chemical Science, 2015, vol. 6, # 8, p. 4978 - 4985]
[20]Kalimuthu, Palraj; Heider, Johann; Knack, Daniel; Bernhardt, Paul V. [Journal of Physical Chemistry B, 2015, vol. 119, # 8, p. 3456 - 3463]
[21]Schliebe, Christian; Pfaff, Ulrike; Gemming, Thomas; Lochenie, Charles; Weber, Birgit; Lang, Heinrich [European Journal of Inorganic Chemistry, 2015, vol. 2015, # 23, p. 3850 - 3860]
[22]Potkin; Dikusar; Kletskov; Petkevich; Semenova; Kolesnik; Zvereva; Zhukovskaya; Rosentsveig; Levkovskaya; Zolotar [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 338 - 343][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 338 - 343,6]
[23]Lewtak, Jan P; Landman, Marilé; Fernández, Israel; Swarts, Jannie C [Inorganic Chemistry, 2016, vol. 55, # 5, p. 2584 - 2596]
[24]Labulo, Ayomide H.; Ngidi, Nonjabulo P.D.; Omondi, Bernard; Nyamori, Vincent O. [Journal of Organometallic Chemistry, 2018, vol. 868, p. 66 - 75]
[25]Singh, Amandeep; Zhang, David; Tam, Christina C.; Cheng, Luisa W.; Land, Kirkwood M.; Kumar, Vipan [Journal of Organometallic Chemistry, 2019, vol. 896, p. 1 - 4] Rani, Anu; Singh, Gurjot Inder; Kaur, Ramandeep; Palma, Gabriella; Perumal, Shanen; Kaur, Mandeep; Ebenezer, Oluwakemi; Awolade, Paul; Singh, Parvesh; Kumar, Vipan [Journal of Organometallic Chemistry, 2020, vol. 907]
[26]Ge, Xingxing; Chen, Shujiao; Liu, Xicheng; Wang, Qinghui; Gao, Lijun; Zhao, Chengfeng; Zhang, Lei; Shao, Mingxiao; Yuan, Xiang-Ai; Tian, Laijin; Liu, Zhe [Inorganic Chemistry, 2019, vol. 58, # 20, p. 14175 - 14184]
[27]Bretner, Maria; Buchowicz, Włodzimierz; Kamiński, Radosław; Koszytkowska-Stawińska, Mariola; Mazur, Maria; Mrozowicz, Michał; Ochal, Zbigniew; Wińska, Patrycja [Dalton Transactions, 2020, vol. 49, # 33, p. 11504 - 11511]
[28]Adarsh, Nayarassery N.; Karmakar, Manisha; Mondal, Bijan; Pal, Adwitiya; Thakur, Arunabha [Inorganic Chemistry, 2021, vol. 60, # 8, p. 6086 - 6098]

4
[ 1273-86-5 ]
chloromethylferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus trichloride In benzene presence of small amt. of pyridine;;
	With acetyl chloride In not given byproducts: CH3COOH;
	With PCl₃ In benzene presence of small amt. of pyridine;;

With oxalyl dichloride In dichloromethane for 4h; Inert atmosphere;

Synthesis of [Pt2(μ-S)(μ-SCH2Fc)(PPh3)4]PF6 3a using FcCH2Cl To a solution of FcCH2OH (250 mg, 1.16 mmol) in dichloromethane(20 mL) was added oxalyl chloride (6 drops, excess) and theresulting solution stirred for 4 h under a nitrogen atmosphere.The volatiles were removed under vacuum, and the resulting solidwas briefly washed with water (10 mL). [Pt2(μ-S)2(PPh3)4](400 mg, 0.266 mmol) and methanol (40 mL) were added, andthe mixture stirred, rapidly forming a greenish solution. Calciumcarbonate (ca. 1 g) was added, whereupon the mixture lightenedto a yellow-orange colour. After stirring for 16 h, the mixturewas filtered, and to the filtrate was added NH4PF6 (200 mg,1.23 mmol). Water (5 mL) was added to assist precipitation ofthe product. The solid was filtered, washed with water (10 mL)and diethyl ether (10 mL), and dried under vacuum to give theproduct as a light orange powder (298 mg, 61%). Crystallisationby vapour diffusion of diethyl ether into a dichloromethane solutionof the complex at room temperature gave orange crystals ofthe bis-dichloromethane solvate 3a 2CH2Cl2. Found: C, 50.6; H,3.7%. C85H75Cl4F6FeP5Pt2S2 requires C, 50.6; H, 3.8%. ESI MS[Pt2(μ-S)(μ-SCH2Fc)(PPh3)4]+ m/z 1702.282 (calculated m/z1702.261). The compound gave virtually indistinguishable31P{1H} and 1H NMR data (in the 0-6 ppm range) to the BPh4 salt3b (vide infra).

Reference： [1][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.2.2, page 381 - 383]
[2]Patin, H.; Roullier, L.; Dabard, R. [Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 272, p. 675 - 678] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.2.2, page 381 - 383]
[3]Schloegl, K. [Monatshefte fur Chemie][Monatshefte fuer Chemie, 1957, vol. 88, p. 601 - 621]
[4]Devoy, Sarah M.; Henderson, William; Nicholson, Brian K. [Inorganica Chimica Acta, 2013, vol. 406, p. 81 - 86]

5
[ 1273-86-5 ]
[ 75-08-1 ]
C₁₀H₉FeCH₂SC₂H₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With [Fe(CO)₂(Cp)][OTf] In dichloromethane at 20℃; for 1h;
60%	With CH₃COOH or CF₃COOH

Reference： [1]Mazzoni, Rita; Salmi, Mauro; Zacchini, Stefano; Zanotti, Valerio [European Journal of Inorganic Chemistry, 2013, # 21, p. 3710 - 3718]
[2]Combs et al. [Journal of Organic Chemistry, 1969, vol. 34, p. 1511] Bublitz, D. E. [Journal of Organometallic Chemistry, 1966, vol. 6, p. 436 - 438] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A5, 5.1.5.3, page 5 - 17]

6
[ 1273-86-5 ]
[ 60-24-2 ]
ferrocenylmethyl 2-hydroxyethylsulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With CH₃COOH or CF₃COOH
91%	With [Fe(CO)₂(Cp)][OTf] In dichloromethane at 20℃; for 1h;

Reference： [1]Combs et al. [Journal of Organic Chemistry, 1969, vol. 34, p. 1511] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A5, 5.1.5.3, page 5 - 17]
[2]Mazzoni, Rita; Salmi, Mauro; Zacchini, Stefano; Zanotti, Valerio [European Journal of Inorganic Chemistry, 2013, # 21, p. 3710 - 3718]
[3]Ratajczak, A.; Misterkiewicz, B.; Czech, B. [Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1977, vol. 25, p. 27 - 33]

7
[ 1273-86-5 ]
[ 123-54-6 ]
3-(ferrocenylmethyl)pentane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With HBF₄ or HClO₄ In dichloromethane byproducts: H2O; aq. HBF4 (45 %) or HClO4 (70 %) added to the Fe-complex and acac, soln.stirred (30 min, 20°C), addn. of ether; ether soln. washed twice (water), dried (sodium sulfate); solvent removed (vac.), recrystn. (hexane);
98%	With tetrafluoroboric acid In dichloromethane; water addn. dropwise of HBF4 (40% in water) to soln. of pentane-2,4-dione and ferrocenylmethanol in CH2Cl2; stirring at room temp. for 1 h; diluting with H2O; extn. with CH2Cl2; drying over Na2SO4, filtration, concn. in vac., as oil;
90%	With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 0.583333h; Inert atmosphere; Schlenk technique;	Synthesis of 3-ferrocenylmethyl-pentane-2,4-dione (1) In a Schlenk tube, 1.00 g (4.63 mmol) of ferrocenyl methanol and 0.47 mL(4.7 mmol) of 2,4 pentanedione were dissolved in 8 mL of acetonitrile at room temperature (rt). After 5 min of stirring, 0.125 g (0.23 mmol) of cerium(IV)ammonium nitrate (5% molar) were added. The reaction mixture was stirred for 30 min at rt and then evaporated under reduced pressure. The solid residue was mixed with 5 mL of water and extracted with 10 mL of dichloromethane.The organic phase was dried over MgSO4, filtered off and evaporated under reduced pressure to afford 1.25 g (4.29 mmol, 90% yield) of 1 as an orange oil.

Reference： [1]Boev, V. I.; Dombrovskii, A. V. [Journal of general chemistry of the USSR, 1984, vol. 54, p. 1660 - 1668][J.Gen.Chem.USSR (Engl.Transl.), 1984, vol. 54, p. 1863 - 1873]
[2]González, Asensio; López, Concepción; Solans, Xavier; Font-Bardía, Mercè; Molins, Elies [Journal of Organometallic Chemistry, 2008, vol. 693, # 12, p. 2119 - 2131]
[3]Ahumada, Guillermo; Roisnel, Thierry; Hamon, Jean-Rene; Carrillo, David; Manzur, Carolina [Journal of the Chilean Chemical Society, 2013, vol. 58, # 4, p. 1963 - 1966]

8
[ 1273-86-5 ]
[ 100-01-6 ]
[N-(p-nitrophenyl)amino]methylferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With HClO₄ or HBF₄ In dichloromethane byproducts: H2O; aq. HClO4 (70 %) or HBF4 added (vigorous stirring) to the Fe-complex and the amine; soln. stirred (60 min, room temp.), addn. of ether; ethereal soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.), recrystn. (heptane); elem. anal.;
92%	With [Fe(CO)₂(Cp)][OTf] In dichloromethane at 20℃; for 1h;
84%	In methanol; water pH=9.7, in boiling CH3OH/H2O;

84%

In methanol; water pH=9.7, in boiling CH3OH/H2O;

Reference： [1]Boev, V. I.; Dombrovskii, A. V. [Journal of general chemistry of the USSR, 1984, vol. 54, p. 1660 - 1668][J.Gen.Chem.USSR (Engl.Transl.), 1984, vol. 54, p. 1863 - 1873]
[2]Mazzoni, Rita; Salmi, Mauro; Zacchini, Stefano; Zanotti, Valerio [European Journal of Inorganic Chemistry, 2013, # 21, p. 3710 - 3718]
[3]Beckwith, A. L. J.; Vickery, G. G. [Journal of the Chemical Society. Perkin transactions I][Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 1818 - 1821]
[4][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.6.4, page 205 - 216]

9
[ 1273-86-5 ]
[ 108-98-5 ]
(ferrocenylmethyl)(phenyl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With tetrafluoroboric acid In dichloromethane; water at 20℃; for 0.0833333h;	1 (Ferrocenylmethyl) (phenyl) sulfane (3a) Synthesis Ferrocenemethanol (2a, 0.020 g, 0.093 mmol) was dissolved in dichloromethane (0.4 mL) thio phenol (0.031 g, Place the 0.28 mmol). Fluoro boric acid solution to the solution put (48 wt%, 0.034 mL, 0.18 mmol). Mixed reactions After stirring for 5 minutes with water at room temperature, poured into a saturated aqueous solution of sodium bicarbonate (5 mL), place a dichloromethane (10 mL) Uh diluted. The organic layer was separated and extracted three times the remaining water layer with dichloromethane (10 mL x 3). Oil collected Group layer is washed with a saturated aqueous sodium chloride solution, placed into the over anhydrous sodium sulfate, filtered under reduced pressure. The solvent of the filtrate under reduced pressure After removing all column chromatography (hexane: ethyl acetate = 30: 1) to give compound 3a as a yellow solid (0.028 g, 98%).
92%	With CF₃COOH or CH₃COOH
88%	With [Fe(CO)₂(Cp)][OTf] In dichloromethane at 20℃; for 1h;

Reference： [1]Current Patent Assignee: DIATECH KOREA CO LTD; SOGANG UNIVERSITY - KR101583811, 2016, B1 Location in patent: Paragraph 0052; 0054; 0073; 0074
[2]Misterkiewicz, B.; Kajdas, C.; Dominiak, M.; Dabrowski, J.; Wasilewski, J. [Chemistry and industry][Chemistry and Industry (London, United Kingdom), 1981, p. 433 - 434] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A5, 5.1.5.3, page 5 - 17]
[3]Mazzoni, Rita; Salmi, Mauro; Zacchini, Stefano; Zanotti, Valerio [European Journal of Inorganic Chemistry, 2013, # 21, p. 3710 - 3718]

10
[ 1273-86-5 ]
[ 104-94-9 ]
[N-(p-methoxyphenyl)amino]methylferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With [N,S-(2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone)RuH(CO)(PPh₃)₂]; potassium hydroxide In toluene at 100℃; for 12h;
70%	In methanol; water pH 9.7;
70%	In water boiling, pH 9.7;

	In ethylene glycol 100 to 130°C, pH 9.7;
	In neat (no solvent) 110°C;

Reference： [1]Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Linert, Wolfgang; Gusev, Alexey [RSC Advances, 2015, vol. 5, # 15, p. 11405 - 11422]
[2]Beckwith, A. L. J.; Vickery, G. G. [Journal of the Chemical Society. Perkin transactions I][Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 1818 - 1821] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.2.2, page 32 - 36]
[3]Beckwith, A. L. J.; Vickery, G. G. [Journal of the Chemical Society. Perkin transactions I][Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 1818 - 1821] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.2.2, page 32 - 36]
[4]Marr, G.; Rockett, B. W.; Rushworth, A. [Journal of the Chemical Society C: Organic][Journal of the Chemical Society [Section] C: Organic, 1971, p. 4000 - 4002] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.2.2, page 32 - 36]
[5]Marr, G.; Rockett, B. W.; Rushworth, A. [Journal of the Chemical Society C: Organic][Journal of the Chemical Society [Section] C: Organic, 1971, p. 4000 - 4002] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.2.2, page 32 - 36]

11
[ 1273-86-5 ]
[ 106-47-8 ]
[N-(p-chlorophenyl)amino]methylferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With [RuCl(CO)(PPh₃)(PNS-Me)]; potassium hydroxide In toluene at 100℃; for 12h;
91%	With [N,S-(2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone)RuH(CO)(PPh₃)₂]; potassium hydroxide In toluene at 100℃; for 12h;
78%	With indium(III) triflate In water at 100℃; for 7h; chemoselective reaction;	4.2 General procedure for the alkylation of indoles, anilines and thiols with enamide General procedure: Amine (1.0mmol), In(OTf)3 (0.1mmol) and anisyl alcohol (1.2mmol) were added into a flask. Then the mixture was vigorously stirred at reflux, until amine was completely consumed as indicated by TLC analysis or 24h. After the completion of reaction, CH2Cl2 (15mL×2) was used to extract the product, the organic layer was dried with anhydrous Na2SO4. Then the solvent was evaporated under the reduced pressure. The residue was purified by flash column chromatography with ethyl acetate and petroleum ether as eluents to afford pure product. This procedure was followed for the synthesis of other N-benzylation amines.

68%	In ethylene glycol 100 to 130°C;
68%	In neat (no solvent) 110°C;

Reference： [1]Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Ramkumar, Venkatachalam [Dalton Transactions, 2014, vol. 43, # 21, p. 7889 - 7902]
[2]Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Linert, Wolfgang; Gusev, Alexey [RSC Advances, 2015, vol. 5, # 15, p. 11405 - 11422]
[3]Yang, Jin-Ming; Jiang, Ran; Wu, Lin; Xu, Xiao-Ping; Wang, Shun-Yi; Ji, Shun-Jun [Tetrahedron, 2013, vol. 69, # 37, p. 7988 - 7994]
[4]Marr, G.; Rockett, B. W.; Rushworth, A. [Journal of the Chemical Society C: Organic][Journal of the Chemical Society [Section] C: Organic, 1971, p. 4000 - 4002] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.2.2, page 32 - 36]
[5]Marr, G.; Rockett, B. W.; Rushworth, A. [Journal of the Chemical Society C: Organic][Journal of the Chemical Society [Section] C: Organic, 1971, p. 4000 - 4002] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.2.2, page 32 - 36]

12
[ 1273-86-5 ]
[ 106-40-1 ]
[ 78637-38-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With HClO₄ or HBF₄ In dichloromethane byproducts: H2O; aq. HClO4 (70 %) or HBF4 (45 %) added (vigorous stirring) to the Fe-complex and the amine; soln. stirred (30 min, room temp.), addn. of ether; ethereal soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.), recrystn. (heptane); elem. anal.;
87%	With [N,S-(2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone)RuH(CO)(PPh₃)₂]; potassium hydroxide In toluene at 100℃; for 12h;
86%	With [RuCl(CO)(PPh₃)(PNS-Me)]; potassium hydroxide In toluene at 100℃; for 12h;

Reference： [1]Boev, V. I.; Dombrovskii, A. V. [Journal of general chemistry of the USSR, 1984, vol. 54, p. 1660 - 1668][J.Gen.Chem.USSR (Engl.Transl.), 1984, vol. 54, p. 1863 - 1873]
[2]Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Linert, Wolfgang; Gusev, Alexey [RSC Advances, 2015, vol. 5, # 15, p. 11405 - 11422]
[3]Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Ramkumar, Venkatachalam [Dalton Transactions, 2014, vol. 43, # 21, p. 7889 - 7902]

13
[ 1273-86-5 ]
[ 312-73-2 ]
[ 227953-88-0 ]

Reference： [1]Journal of Organometallic Chemistry,1999,vol. 580,p. 26 - 35

14
[ 271-44-3 ]
[ 1273-86-5 ]
[ 521943-96-4 ]
[ 521943-94-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 46% 2: 41%	With HBF₄; NH₃ In chloroform; water monomer addn. of aq. soln. of HBF4 with vigorous stirring to mixt. of indazole and (C5H5Fe(C5H4CH2OH) in CHCl3; stirring for 5 min; addn. of distd. water and aq. ammonia; addn. of ether, sepn. of org. layer, evapn. of solvent in air, dissolving in CHCl3, chromy. on Al2O3; elution with benzene; removal of solvent; elution with chloroform, removal of solvent, recrystn. from hexane;
1: 37% 2: 33%	With hydrogen tetrafluoroborate In dichloromethane; water monomer at 20℃; for 1h;	Synthesis of 1-N-ferrocenylmethyl- and 2-N-ferrocenylmethylindazoles (1 and 2). To a solution of indazole (2.50 g, 0,021 mol) in CH2Cl2 (100 ml) ferrocenylmethanol (4.58 g, 0.021 mol), water (8 ml) and 48% HBF4 (12 ml) were added. The mixture was stirred for 1 h, diluted with water, basified with sodium hydroxide solution to pH 10, extracted with CH2Cl2, washed with water and brine, dried over Na2SO4 and evaporated. The residue was purified by SiO2 column chromatography with AcOEt/petroleum ether (1:9) to afford 1 and 2. 1: 2.47 g (37%). Yellow powder, m. p. 137-138° C. Rf = 0.54 (light petroleum ether/AcOEt = 4:1). Anal.: C, 68.01; H, 5.41; Fe, 17.5; N, 8.49%. Calc. for C18H16FeN2: C, 68.38; H, 5.10; Fe, 17.66; N, 8.86%. IR (KBr, ν, cm-1): 1106, 1000, 820, 491, 481 ( C5H5FeC5H4). EI-MS, m/z (RI, %): 316 [ M]+ (100). 1H NMR (500 MHz, CDCl3) δ 8.01 (s, 1H, H3), 7.74 (d, J = 8.1 Hz, 1H, H4), 7.49 (d, J = 8.4 Hz, 1H, H7), 7.39 (t, J = 7.7 Hz, 1H, H6), 7.15 (t, J = 7.3 Hz, 1H, H5), 5.35 (s, 2H, CH2), 4.34 - 4.29 (m, 2H, C5H4), 4.19 (s, 5H, C5H5), 4.16 - 4.12 (m, 2H, C5H4). 13C NMR (126 MHz, CDCl3) δ 139.0 (C8), 132.8 (C3), 126.1 (C6), 124.2 (C9), 121.1 (C4), 120.5 (C5), 109.3 (C7), 83.7 (ipso-C5H4), 68.8 ( C5H5), 68.7 ( C5H4), 68.3 ( C5H4), 48.8 ( CH2). 2: 2.20 g (33%). Yellow powder, m. p. 166-167° C. Rf = 0.39 (light petroleum ether/AcOEt = 4:1). Anal.: C, 68.39; H, 5.27; Fe, 17.0; N, 8.61%. Calc. for C18H16FeN2: C, 68.38; H, 5.10; Fe, 17.66; N, 8.86%. IR (KBr, ν, cm-1): 1102, 1001, 817, 500, 482 ( C5H5FeC5H4). EI-MS, m/z (RI, %): 316 [ M]+ (100). 1H NMR (500 MHz, CDCl3) δ 7.84 (s, 1H, H3), 7.72 (d, J = 8.8 Hz, 1H, H7), 7.61 (d, J = 8.4 Hz, 1H, H4), 7.31 - 7.25 (m, 1H, H6), 7.10 - 7.04 (m, 1H, H5), 5.39 (s, 2H, CH2), 4.40 - 4.36 (m, 2H, C5H4), 4.24 (t, J = 1.8 Hz, 2H, C5H4), 4.22 (s, 5H, C5H5). 13C NMR (126 MHz, CDCl3) δ 148.6 (C8), 125.8 (C6), 121.8 (C9), 121.7 (C3), 121.5 (C5), 120.2 (C4), 117.5 (C7), 81.6 (ipso- C5H4), 69.3 ( C5H4), 69.0 ( C5H4), 68,9 ( C5H5), 53.4 ( CH2).
1: 37% 2: 33%	With hydrogen tetrafluoroborate In dichloromethane; water monomer at 20℃; for 1h;	Synthesis of 1-N-ferrocenylmethyl- and 2-N-ferrocenylmethylindazoles (1 and 2). To a solution of indazole (2.50 g, 0,021 mol) in CH2Cl2 (100 ml) ferrocenylmethanol (4.58 g, 0.021 mol), water (8 ml) and 48% HBF4 (12 ml) were added. The mixture was stirred for 1 h, diluted with water, basified with sodium hydroxide solution to pH 10, extracted with CH2Cl2, washed with water and brine, dried over Na2SO4 and evaporated. The residue was purified by SiO2 column chromatography with AcOEt/petroleum ether (1:9) to afford 1 and 2. 1: 2.47 g (37%). Yellow powder, m. p. 137-138° C. Rf = 0.54 (light petroleum ether/AcOEt = 4:1). Anal.: C, 68.01; H, 5.41; Fe, 17.5; N, 8.49%. Calc. for C18H16FeN2: C, 68.38; H, 5.10; Fe, 17.66; N, 8.86%. IR (KBr, ν, cm-1): 1106, 1000, 820, 491, 481 ( C5H5FeC5H4). EI-MS, m/z (RI, %): 316 [ M]+ (100). 1H NMR (500 MHz, CDCl3) δ 8.01 (s, 1H, H3), 7.74 (d, J = 8.1 Hz, 1H, H4), 7.49 (d, J = 8.4 Hz, 1H, H7), 7.39 (t, J = 7.7 Hz, 1H, H6), 7.15 (t, J = 7.3 Hz, 1H, H5), 5.35 (s, 2H, CH2), 4.34 - 4.29 (m, 2H, C5H4), 4.19 (s, 5H, C5H5), 4.16 - 4.12 (m, 2H, C5H4). 13C NMR (126 MHz, CDCl3) δ 139.0 (C8), 132.8 (C3), 126.1 (C6), 124.2 (C9), 121.1 (C4), 120.5 (C5), 109.3 (C7), 83.7 (ipso-C5H4), 68.8 ( C5H5), 68.7 ( C5H4), 68.3 ( C5H4), 48.8 ( CH2). 2: 2.20 g (33%). Yellow powder, m. p. 166-167° C. Rf = 0.39 (light petroleum ether/AcOEt = 4:1). Anal.: C, 68.39; H, 5.27; Fe, 17.0; N, 8.61%. Calc. for C18H16FeN2: C, 68.38; H, 5.10; Fe, 17.66; N, 8.86%. IR (KBr, ν, cm-1): 1102, 1001, 817, 500, 482 ( C5H5FeC5H4). EI-MS, m/z (RI, %): 316 [ M]+ (100). 1H NMR (500 MHz, CDCl3) δ 7.84 (s, 1H, H3), 7.72 (d, J = 8.8 Hz, 1H, H7), 7.61 (d, J = 8.4 Hz, 1H, H4), 7.31 - 7.25 (m, 1H, H6), 7.10 - 7.04 (m, 1H, H5), 5.39 (s, 2H, CH2), 4.40 - 4.36 (m, 2H, C5H4), 4.24 (t, J = 1.8 Hz, 2H, C5H4), 4.22 (s, 5H, C5H5). 13C NMR (126 MHz, CDCl3) δ 148.6 (C8), 125.8 (C6), 121.8 (C9), 121.7 (C3), 121.5 (C5), 120.2 (C4), 117.5 (C7), 81.6 (ipso- C5H4), 69.3 ( C5H4), 69.0 ( C5H4), 68,9 ( C5H5), 53.4 ( CH2).

Reference： [1]Gumenyuk; Starikova; Nekrasov; Babin [Russian Chemical Bulletin, 2002, vol. 51, # 10, p. 1894 - 1899]
[2]Bulygina, Ludmila A.; Khrushcheva, Natalya S.; Lyssenko, Konstantin A.; Anisimov, Alexey A.; Peregudov, Aleksander S. [Transition Metal Chemistry, 2022, vol. 47, # 1, p. 39 - 46]
[3]Bulygina, Ludmila A.; Khrushcheva, Natalya S.; Lyssenko, Konstantin A.; Anisimov, Alexey A.; Peregudov, Aleksander S. [Transition Metal Chemistry, 2022, vol. 47, # 1, p. 39 - 46]

15
[ 207301-19-7 ]
[ 1273-86-5 ]
[ 16687-60-8 ]

Reference： [1]Russian Journal of General Chemistry,1997,vol. 67,p. 1299 - 1305

16
tetrafluoroboric acid [ No CAS ]
[ 1273-86-5 ]
[ 16687-60-8 ]
[ 207301-19-7 ]

Reference： [1]Russian Journal of General Chemistry,1997,vol. 67,p. 1299 - 1305

17
[ 1287-16-7 ]
[ 80937-33-3 ]
[ 12093-10-6 ]
[ 1271-42-7 ]
[ 1273-86-5 ]
[ 124-38-9 ]
[ 364040-28-8 ]

Reference： [1]Russian Journal of General Chemistry,2009,vol. 79,p. 2304 - 2316
[2]Russian Journal of General Chemistry,2009,vol. 79,p. 2304 - 2316
[3]Russian Journal of General Chemistry,2009,vol. 79,p. 2304 - 2316

18
[ 1287-16-7 ]
[ 80937-33-3 ]
[ 12093-10-6 ]
[ 1273-86-5 ]
[ 124-38-9 ]

Reference： [1]Russian Journal of General Chemistry,2009,vol. 79,p. 2304 - 2316
[2]Russian Journal of General Chemistry,2009,vol. 79,p. 2304 - 2316
[3]Russian Journal of General Chemistry,2009,vol. 79,p. 2304 - 2316
[4]Russian Journal of General Chemistry,2009,vol. 79,p. 2304 - 2316

19
[ 1273-86-5 ]
[ 106-96-7 ]
[ 143453-58-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydride In N,N-dimethyl-formamide; toluene; mineral oil at 0 - 20℃; for 3h; Inert atmosphere;
83%	With sodium hydride In N,N-dimethyl-formamide; toluene at 0 - 20℃; for 4h;
83%	With sodium hydride In N,N-dimethyl-formamide; toluene for 4h;

81%	With sodium hydride In tetrahydrofuran at 20℃;
50%	With NaOH In dimethyl sulfoxide under Ar/N2, Schlenk techniques and glove box; soln. of (C5H5)Fe(C5H4CH2OH) (2.3 mmol) treated with NaOH (2.76 mmol) at room temp. for 30 min, CHCCH2Br (3.45 mmol) added dropwise, stirred for 24 h; diluted with cold H2O, extracted with EtOAc, organic layer dried over Na2SO4, solvent removed (vac.), chromd. (silica gel, EtOAc/hexane 25:75 v/v eluent); elem. anal.;
	With sodium hydride at 80℃; for 8h;
	With sodium hydride In N,N-dimethyl-formamide at 80℃; for 4h;
	With sodium hydride In N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere;

Reference： [1]Yamamoto, Kosuke; Bruun, Theodora; Kim, Jung Yun; Zhang, Lei; Lautens, Mark [Organic Letters, 2016, vol. 18, # 11, p. 2644 - 2647]
[2]Rajakumar, Perumal; Anandhan, Ramasamy; Kannan, Ayyavoo [Australian Journal of Chemistry, 2012, vol. 65, # 10, p. 1457 - 1462]
[3]Rajakumar, Perumal; Kannan, Ayyavoo; Anandhan, Ramasamy [New Journal of Chemistry, 2014, vol. 38, # 4, p. 1594 - 1600]
[4]Lim, Byung Joon; Hwang, Inhong; Ellington, Andrew D.; Sessler, Jonathan L. [Helvetica Chimica Acta, 2019, vol. 102, # 2]
[5]Thakur, Arunabha; Adarsh; Chakraborty, Amarnath; Devi, Manjula; Ghosh, Sundargopal [Journal of Organometallic Chemistry, 2010, vol. 695, # 7, p. 1059 - 1064]
[6]Singh, Amandeep; Zhang, David; Tam, Christina C.; Cheng, Luisa W.; Land, Kirkwood M.; Kumar, Vipan [Journal of Organometallic Chemistry, 2019, vol. 896, p. 1 - 4]
[7]Rani, Anu; Singh, Gurjot Inder; Kaur, Ramandeep; Palma, Gabriella; Perumal, Shanen; Kaur, Mandeep; Ebenezer, Oluwakemi; Awolade, Paul; Singh, Parvesh; Kumar, Vipan [Journal of Organometallic Chemistry, 2020, vol. 907]
[8]Adarsh, Nayarassery N.; Karmakar, Manisha; Mondal, Bijan; Pal, Adwitiya; Thakur, Arunabha [Inorganic Chemistry, 2021, vol. 60, # 8, p. 6086 - 6098]

20
[ 1273-86-5 ]
[ 69661-83-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With [Fe(CO)₂(Cp)][OTf]; N-butylamine In dichloromethane at 20℃; for 16h;
	With Nafion film In carbon dioxide Nafion film and FcCH2OH were taken, reacted under 20MPa and 80°C; After opening the cell crystals was afforded; 1H NMR and X-Ray;
	With ClB(C₈H₄N₂)3 In toluene under Ar atm. using Schlenk techniques; prepn. in boiling toluene;

With phosphorus tribromide In tetrahydrofuran; water at 0 - 20℃;

Reference： [1]Mazzoni, Rita; Salmi, Mauro; Zacchini, Stefano; Zanotti, Valerio [European Journal of Inorganic Chemistry, 2013, # 21, p. 3710 - 3718]
[2]Sokolov, Viatcheslav I.; Nikitin, Lev N.; Bulygina, Ludmila A.; Khrustalev, Victor N.; Starikova, Zoya A.; Khokhlov, Alexei R. [Journal of Organometallic Chemistry, 2010, vol. 695, # 6, p. 799 - 803]
[3]Solntsev, Pavlo V.; Spurgin, Katelynn L.; Sabin, Jared R.; Heikal, Ahmed A.; Nemykin, Victor N. [Inorganic Chemistry, 2012, vol. 51, # 12, p. 6537 - 6547]
[4]Gharib, Bhasem; Hirsch, Andreas [European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4123 - 4136]

21
[ 1273-86-5 ]
[ 90357-51-0 ]
[ 1283675-92-2 ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1049 - 1056

22
[ 13228-40-5 ]
[ 1273-86-5 ]
[ 1283109-38-5 ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1011 - 1017

23
[ 616-47-7 ]
ammonium hexafluorophosphate [ No CAS ]
[ 1273-86-5 ]
[ 260357-19-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 1-methyl-1H-imidazole; 1-ferrocenylmethanol With acetic acid at 60℃; for 5h; Inert atmosphere; Schlenk technique; Stage #2: ammonium hexafluorophosphate In ethanol at 20℃; for 2h; Inert atmosphere; Schlenk technique;	Preparation of receptor 1-(ferrocenylmethyl)-3-methylimidazolium hexafluorophosphate (1b). General procedure: Under a nitrogen atmosphere, ferrocenyl methanol (216 mg, 1 mmol) and 1-methylimidazole (240 mg, 3 mmol) were dissolved in 3 mL of acetic acid and stirred for 5 h at 60 °C. Volatiles were evaporated, and a solution of NH4PF6 (1.11 g, 6.2 mmol) in EtOH (5 mL) was added. After the solution had been stirred for 2 h at room temperature, the solvent was evaporated. CH2Cl2 was added to the solution, and the solution was filtered through Celite. The solvent was removed, and the residues were recrystallization from acetone/ether afforded 0.30 g (71% yield) of 1b as yellow needles. 1H NMR (600 MHz, CD3COCD3): δ (ppm) 4.08 (s, 3H, CH3), 4.26 (s, 5H, C5H5), 4.33 (s, 2H, C5H4), 4.54 (s, 2H, C5H4), 5.44 (s, 2H, CH2), 7.71 (s, 1H, CH=CH), 7.76 (s, 1H, CH=CH), 9.01 (s, 1H, NCH=N). 13C NMR (400MHz, CD3COCD3): δ (ppm) 36.92 (CH3), 50.13 (CH2), 69.56, 69.96, 70.10, 80.54 (Cp-C), 122.87, 124.54, 136.59 (imidazole-C).

Reference： [1]Kong, Dandan; Weng, Tanqing; He, Wenxue; Liu, Bin; Jin, Shan; Hao, Xiao; Liu, Shenghua [Journal of Organometallic Chemistry, 2013, vol. 727, p. 19 - 27]

24
[ 1273-86-5 ]
[ 83-72-7 ]
2-hydroxy-3-[(ferrocenyl)methyl]-1,4-naphthoquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 0.166667h; Green chemistry;
65%	In water at 40℃; for 23h;	4.5 Synthesis of 3-(ferrocenylmethyl)-2-hydroxy-1,4-naphthoquinones derivatives 10 General procedure: To a clean and dry round bottom flask containing 3-5mmol of the ferrocenylcarbinol, an equivalent quantity of 2-hydroxy-1,4-naphthoquinone and 20mL of water were added. The mixture was stirred and heated at 40°C or 70°C; the formation of a green solid in the walls of the flask was observed. Reaction was stopped when no change was detected by TLC, reaction time was variable depending on the product. The mixture was extracted with MTBE and the combined organic phase was dried over anhydrous sodium sulfate. The solvent was removed and the crude product (red to orange solid) was purified by column chromatography column on silica gel (230-400mesh) with a gradient of cyclohexane-benzene as eluent, obtaining green solids.

Reference： [1]Chen, Yixin; Wang, Yurong; Zhong, Rong; Li, Jinshan [Journal of Organic Chemistry, 2020, vol. 85, # 16, p. 10638 - 10647]
[2]García-Barrantes, Pedro M.; Lamoureux, Guy V.; Pérez, Alice L.; García-Sánchez, Rory N.; Martínez, Antonio R.; San Feliciano, Arturo [European Journal of Medicinal Chemistry, 2013, vol. 70, p. 548 - 557]

25
[ 1273-86-5 ]
1,1,1,5,5,5-hexafluoropentan-3-ol [ No CAS ]
((1,1,1,3,3,3-hexafluoropropan-2-yloxy)methyl)ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	at 50℃; for 18h;	General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottomflask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored byTLC and capillary electrophoresis, after completion of reaction. The reactionmixture was flash chromatographed by silica gel column to give the purecompounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.
80%	at 50℃; for 18h;	General procedure: General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottom flask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored by TLC and capillary electrophoresis, after completion of reaction. The reaction mixture was flash chromatographed by silica gel column to give the pure compounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.

Reference： [1]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2014, vol. 55, # 4, p. 869 - 872]
[2]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2015, vol. 55, # 4, p. 869 - 872]

26
[ 95335-91-4 ]
[ 1273-86-5 ]
[ 1551616-52-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	at 90℃; for 15h;	General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottomflask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored byTLC and capillary electrophoresis, after completion of reaction. The reactionmixture was flash chromatographed by silica gel column to give the purecompounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.
98%	at 90℃; for 15h;	General procedure: General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottom flask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored by TLC and capillary electrophoresis, after completion of reaction. The reaction mixture was flash chromatographed by silica gel column to give the pure compounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.

Reference： [1]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2014, vol. 55, # 4, p. 869 - 872]
[2]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2015, vol. 55, # 4, p. 869 - 872]

27
[ 1273-86-5 ]
[ 534-03-2 ]
[ 1551616-66-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,1,1,3',3',3'-hexafluoro-propanol at 90℃; for 8h;	General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottomflask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored byTLC and capillary electrophoresis, after completion of reaction. The reactionmixture was flash chromatographed by silica gel column to give the purecompounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.

Reference： [1]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2014, vol. 55, # 4, p. 869 - 872]

28
[ 1273-86-5 ]
[ 496834-01-6 ]
[ 1551616-69-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; for 8h;	General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottomflask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored byTLC and capillary electrophoresis, after completion of reaction. The reactionmixture was flash chromatographed by silica gel column to give the purecompounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.

Reference： [1]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2014, vol. 55, # 4, p. 869 - 872]

29
[ 1273-86-5 ]
[ 112-60-7 ]
[ 1240401-49-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; for 4h;	General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottomflask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored byTLC and capillary electrophoresis, after completion of reaction. The reactionmixture was flash chromatographed by silica gel column to give the purecompounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.
92%	With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; for 4h;	General procedure: General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottom flask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored by TLC and capillary electrophoresis, after completion of reaction. The reaction mixture was flash chromatographed by silica gel column to give the pure compounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.

Reference： [1]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2014, vol. 55, # 4, p. 869 - 872]
[2]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2015, vol. 55, # 4, p. 869 - 872]

30
[ 1273-86-5 ]
[ 4985-46-0 ]
C₂₀H₂₂FeN₂O₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2953 - 2959

31
[ 1273-86-5 ]
[ 106-49-0 ]
[ 170379-54-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium hydroxide In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube;	13 Example 13: Hydrogen Transfer Reaction of Ferrocene Methanol and 4-Methylaniline Catalyzed by Carbon Supported Rhodium Nanomaterials Ferrocenemethanol (1.3 mmol), 4-methylaniline (1 mmol), carbon-supported ruthenium nanomaterial (20 mg),Potassium hydroxide (20 mg) was added to a 25 ml reaction tube with a magnetic stirrer.After repeated nitrogen suction three times, toluene (3 ml) was added via a syringe and then sealed and reacted at 110°C for 24 hours.After the reaction is completed, the catalyst is removed by filtration, and the filtrate is extracted by adding water and ethyl acetate, and the organic phases are combined.After drying, filtration, concentration under reduced pressure, and silica gel column chromatography, N-(ferrocenyl)aniline (yield 85%) was obtained.
68%	With [RuCl(CO)(PPh₃)(PNS-Me)]; potassium hydroxide In toluene at 100℃; for 12h;
	With potassium hydroxide In toluene at 110℃; for 24h; Inert atmosphere;

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN107954879, 2018, A Location in patent: Paragraph 0060
[2]Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Ramkumar, Venkatachalam [Dalton Transactions, 2014, vol. 43, # 21, p. 7889 - 7902]
[3]Guo, Bin; Li, Hong-Xi; Zhang, Shi-Qi; Young, David James; Lang, Jian-Ping [ChemCatChem, 2018, vol. 10, # 24, p. 5627 - 5636]

32
[ 1273-86-5 ]
1,3-dihydroxy-2-propylhydroxylamine [ No CAS ]
[2-ferrocenylmethylamino]-1,3-propanediol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; for 8h;	General procedure: General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottom flask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored by TLC and capillary electrophoresis, after completion of reaction. The reaction mixture was flash chromatographed by silica gel column to give the pure compounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.

Reference： [1]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2015, vol. 55, # 4, p. 869 - 872]

33
[ 1273-86-5 ]
[ 496834-01-6 ]
[3-ferrocenylmethylamino]-1,2-propanediol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; for 8h;	General procedure: General procedure: ferrocenemethanol was added to the substrates 1a-l in a round bottom flask and the mixture was heated under stirring at 50-90°C (as reported in Table 1), the reaction was monitored by TLC and capillary electrophoresis, after completion of reaction. The reaction mixture was flash chromatographed by silica gel column to give the pure compounds 3a-l as reported in Table 1. Typical eluent: hexane/ethyl acetate= 7/3.

Reference： [1]Shisodia, Suresh Udhavrao; Auricchio, Sergio; Citterio, Attilio; Grassi, Marco; Sebastiano, Roberto [Tetrahedron Letters, 2015, vol. 55, # 4, p. 869 - 872]

34
[ 1273-86-5 ]
[ 74-99-7 ]
[ 301205-64-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium hydroxide semihydrate In dimethyl sulfoxide at 80℃; for 2h;	General procedure for the reaction of ferrocenylalkanols 1a,bwith propyne in the KOH/DMSO system General procedure: Method A (Table 2, entries 1,4). Into a glass 50-mL flask equipped with a stirrer, a reflux condenser,a thermometer, a bubbler for propyne supply, and a gasoutlet, alcohol 1a,b (5.0 mmol), KPO0.5O2P (0.16 g, 2.5 mmol),and DMSO (30 mL) were placed. Propyne was passed on stirring for2 h through the reaction mixture heated up to 80 C. After coolingto room temperature the reaction mixture was diluted with anaqueous 1% solution of NH4Cl (50 mL) and extracted with ether(530 mL), the extracts were washed from DMSO by water(230 mL), dried over Na2SO4. Column chromatography (basicAl2O3, eluent hexane/diethyl ether with gradient from 1:0 to 3:1) ofthe crude residue after removal of the solvent gave the pure adducts2c,d and unreacted alcohols 1a,b.
65%	With potassium hydroxide In dimethyl sulfoxide at 70 - 80℃;

Reference： [1]Trofimov, Boris A.; Oparina, Ludmila A.; Tarasova, Olga A.; Artem'ev, Alexander V.; Kobychev, Vladimir B.; Gatilov, Yuriy V.; Albanov, Alexander I.; Gusarova, Nina K. [Tetrahedron, 2014, vol. 70, # 35, p. 5954 - 5960]
[2]Kolyvanov, Nikita A.; Oparina, Ludmila A.; Tarasova, Olga A.; Albanov, Alexander I.; Gusarova, Nina K.; Trofimov, Boris A. [Tetrahedron Letters, 2020, vol. 61, # 28]

35
[ 1273-86-5 ]
[ 74-86-2 ]
(vinyloxy)methylferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium hydroxide semihydrate In dimethyl sulfoxide at 70℃; for 1h; Autoclave;	General procedure for vinylation of ferrocenylalkanols 1a,bwith acetylene General procedure: Method A (Table 1, entries 4, 5). A mixture of alcohol1a,b (30 mmol) and KPO0.5O2P (0.20 g, 3 mmol) in DMSO(50 mL) was placed into a 0.3-L Parr-reactor. The latter was fed withacetylene and then decompressed to atmospheric pressure toremove air. The autoclave was fed with acetylene again (initialpressure at ambient temperature was 13 atm) and heated (70 C)upon stirring for 0.75 or 1 h. The reaction mixture, after cooling toroom temperature, was diluted with an aqueous 1% solution ofNH4Cl (50 mL). The aqueous layer was extracted with diethyl ether(20 mL6), the extracts were washed with water (15 mL3) anddried (Na2SO4). Column chromatography (basic Al2O3, eluent hexane/diethyl ether with gradient from 1:0 to 1:1) of the crude residueafter removal of the solvent gave the pure adducts 2a,b andunreacted alcohols 1a,b.
81%	With potassium hydroxide In dimethyl sulfoxide at 70 - 80℃;
	With potassium hydroxide In dimethyl sulfoxide

Reference： [1]Trofimov, Boris A.; Oparina, Ludmila A.; Tarasova, Olga A.; Artem'ev, Alexander V.; Kobychev, Vladimir B.; Gatilov, Yuriy V.; Albanov, Alexander I.; Gusarova, Nina K. [Tetrahedron, 2014, vol. 70, # 35, p. 5954 - 5960]
[2]Kolyvanov, Nikita A.; Oparina, Ludmila A.; Tarasova, Olga A.; Albanov, Alexander I.; Gusarova, Nina K.; Trofimov, Boris A. [Tetrahedron Letters, 2020, vol. 61, # 28]
[3]Oparina, Ludmila A.; Artem'ev, Alexander V.; Vysotskaya, Oksana V.; Tarasova, Olga A.; Shagun, Vladimir A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A. [Tetrahedron, 2016, vol. 72, # 29, p. 4414 - 4422]

36
[ 1273-86-5 ]
[ 55-21-0 ]
N-(ferrocenylmethyl)benzene-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In toluene at 130℃; for 12h;	14 Ν-(Ferrocenemethyl)benzamide The benzonitrile (103mg, 1mmol), [(IPr) AuNTf] (17mg, 0.02mmol, 2mol%),tetrahydrofuran (0.5ml), H 2O (0.5ml) were successively added to the reaction flask25mlSchlenk. After the mixture was reacted at 130 °C at 12 hours, cooled to roomtemperature, the solvent was removed in vacuo under reduced pressure. The [Cp * IrCl 2]2(8mg, 0.01mmol, 1mol%), ferrocene methanol (260mg, 1.2mmol), cesium carbonate (65mg,0.2equiv.) And toluene (1ml) was added to the reaction flask and the reaction mixturewas continued at 130 °C at 12 hours, cooled to room temperature. The solvent was removedrotary evaporation, then purified by column chromatography (developing solvent: ethylacetate / petroleum ether) to give pure title compound Yield: 83%.
	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In toluene at 130℃; for 12h;

Reference： [1]Current Patent Assignee: NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105820061, 2016, A Location in patent: Paragraph 0090-0093
[2]Li, Feng; Ma, Juan; Lu, Lei; Bao, Xiaofeng; Tang, Wanying [Catalysis science and technology, 2015, vol. 5, # 3, p. 1953 - 1960]

37
[ 1273-86-5 ]
3-fluoro-4-(trifluoromethyl)benzonitrile [ No CAS ]
3-(ferrocenyloxy)-4-(trifluoromethyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	Stage #1: 1-ferrocenylmethanol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Schlenk technique; Stage #2: 3-fluoro-4-(trifluoromethyl)benzonitrile In tetrahydrofuran at 0 - 20℃; Schlenk technique;	4.a 3- (Ferrocenyloxy)-4-(trifluoromethyl)benzonitrile (1 ) 3- (Ferrocenyloxy)-4-(trifluoromethyl)benzonitrile (1 ) Ferrocenemethanol (0.19 g, 0.46 mmol) was dissolved in dry THF (40 mL). The solution was cooled with an ice bath to 0°C. Then NaH (16.8 mg, 0.7 mmol) were added and the reaction mixture was stirred for half an hour at 0°C. 3-fluoro-4-(trifluoromethyl)benzonitrile (0.096 g, 0.51 mmol) was added and the reaction mixture was allowed to warm to room temperature. The yellow reaction mixture was stirred overnight at room temperature. After stirring the mixture overnight, additional 3-fluoro-4-(trifluoromethyl) benzonitrile (0.198 g, 1.02 mmol) was added. The reaction was stirred for an additional 24 h at room temperature and then quenched with H20 (1 mL). The organic layer was evaporated under reduced pressure. The remaining residue was redissolved in CH2CI2 (20 mL) and was washed with H20 (5 mL) and brine (2 x 10 mL). The combined aqueous phases were extracted with CH2CI2 (10 mL). The combined organic phases were dried over MgS04, filtered and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica with hexane:ethyl acetate (15:1 ) as the eluent (Rf = 0.42) to afford 3-(ferrocenyloxy)-4-(trifluoromethyl)benzonitrile (1 ) as a bright yellow solid. Yield: 16%. Elemental Analysis: calcd. for Ci9H14F3NOFe = C, 59.25; H, 3.66; N, 3.64. Found = C, 59.07; H, 3.57; N, 3.51. ESI-MS: m/z (%) = 385.05 ([M]+, 100.
16%	Stage #1: 1-ferrocenylmethanol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Schlenk technique; Stage #2: 3-fluoro-4-(trifluoromethyl)benzonitrile In tetrahydrofuran at 20℃; Schlenk technique;

Reference： [1]Current Patent Assignee: UNIVERSITY OF MELBOURNE; UNIVERSITY OF ZURICH - WO2015/44397, 2015, A1 Location in patent: Page/Page column 80-83
[2]Hess, Jeannine; Patra, Malay; Rangasamy, Loganathan; Konatschnig, Sandro; Blacque, Olivier; Jabbar, Abdul; Mac, Patrick; Jorgensen, Erik M.; Gasser, Robin B.; Gasser, Gilles [Chemistry - A European Journal, 2016, vol. 22, # 46, p. 16602 - 16612]

38
[ 1273-86-5 ]
[ 140-29-4 ]
2-phenyl-3-(ferrocenemethyl-2-yl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide In tert-Amyl alcohol at 130℃; for 2h; Microwave irradiation;
79%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide at 130℃; for 2h; Microwave irradiation; Green chemistry;	11 Example 11: 2-Phenyl-3- (2-ferrocenyl) propanamide A solution of cyanobenzyl cyanide (117 mg, 1 mmol)Ferrocene methanol (238 mg, 1.1 mmol)[Rh (cod) Cl] 2 (4.9 mg, 0.01 mmol, 1 mol%),Triphenylphosphine (26 mg, 0.1 mmol, 10 mol%),Potassium hydroxide (22 mg, 0.4 mmol, 40 mol%) were sequentially added to a 10 ml microwave reaction tube.The mixture was reacted at 130 ° C for 2 hours,Cool to room temperature. The solvent was removed by rotary evaporation and then the title compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether) in a yield of 79%.

Reference： [1]Li, Feng; Zou, Xiaoyuan; Wang, Nana [Advanced Synthesis and Catalysis, 2015, vol. 357, # 7, p. 1405 - 1415]
[2]Current Patent Assignee: NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105985256, 2016, A Location in patent: Paragraph 0071; 0072; 0073; 0074; 0075

39
[ 1273-86-5 ]
[ 63-74-1 ]
4-amino-N-(ferrocenemethyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In tert-Amyl alcohol at 120℃; for 12h; Inert atmosphere; Schlenk technique;
80%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In tert-Amyl alcohol at 120℃; for 12h; Inert atmosphere; Schlenk technique;	13 4-amin-N-(ferrocenemethyl)benzenesulfonamide Under a nitrogen atmosphere, 4-aminobenzenesulfonamide (172 mg, 1 mmol)[Cp * IrCl2] 2 (8 mg, 0.01 mmol, 1 mol%),Cesium carbonate (65 mg, 0.2 mmol),Ferrocene methanol (259 mg, 1.2 mmol)Tert-amyl alcohol (1.0 mL) was added sequentially to a 25 mL Schlenk reaction flask.The mixture was allowed to react at 120 ° C for 12 hours,Cooled to room temperature,The solvent was removed under vacuum.And then passed through a column chromatography (developing solvent: ethyl acetate / n-hexane)To pure target compound, yield: 80%.

Reference： [1]Lu, Lei; Ma, Juan; Qu, Panpan; Li, Feng [Organic Letters, 2015, vol. 17, # 10, p. 2350 - 2353]
[2]Current Patent Assignee: NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106146358, 2016, A Location in patent: Paragraph 0081-0084

40
[ 1273-86-5 ]
[ 134469-07-1 ]
N-ferrocenylmethyl-2-thio benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With trifluoroacetic acid In acetone at 20℃; regioselective reaction;	Syntheses General procedure: To a solution of ferrocenylcarbinol, FcCHR(OH), (1.0 mmol) and 2-thiobenzimidazole (1.0 mmol) in acetone (5.0 ml) two drops of trifluoroacetic acid were added. The reaction mixture was stirred overnight until the residue was formed. Then the residue was filtered, washed with cold ether (2 x 20 ml) and dried in vacuo over CaCl2. N-ferrocenylmethyl-2-thio-benzoimidazole (3a) Yield 74%. Yellow powder, m.p. 198-200°С. Anal.: С 60.81; Н 4.77; N 7.81; S 8.76%. Calc. for С18Н16FeN2S: С 60.52; Н 4.80; N 7.84; S 8.98%. EI-MS, m/z (RI, %): 348 [M]+ (83). 1Н NMR (CDCl3, δ, ppm): 4.11 (s, 2H, Fc); 4.25 (s, 5H, Fc); 4.49 (s, 2H, Fc); 5.28 (s, 2H, CH2); 7.15-7.22 (m, 4H, Het); 10.43 (s, 1H, SH). 13C NMR (CDCl3, δ, ppm): 51.7 (CH2), 66.3 (C5H4), 66.9 (C5H4), 69.3 (C5H4), 69.7 (C5H5), 86.9 (ipso-C5H4), 109.9 (Het, C-5), 111.7 (Het, C-6), 122.8 (Het, C-4), 123.2 (Het, C-7), 128.9 (Het, C-9), 131.0 (Het, C-8), 166.7 (C-S).

Reference： [1]Rodionov, Alexey N.; Zherebker, Kira Ya.; Snegur, Lubov V.; Korlyukov, Alexander A.; Arhipov, Dmitry E.; Peregudov, Alexander S.; Ilyin, Mikhail M.; Nikitin, Oleg M.; Morozova, Nataliya B.; Simenel, Alexander A. [Journal of Organometallic Chemistry, 2015, vol. 783, p. 83 - 91]

41
[ 1273-86-5 ]
[ 149-30-4 ]
3-ferrocenylmethylbenzo[d]thiazole-2(3H)thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With tetrafluoroboric acid In dichloromethane; water at 20℃; for 0.0833333h; regioselective reaction;	Syntheses General procedure: To a mixture of 1.0 mmol of ferrocenylcarbinol and 1.0 mmol of the corresponding heterocycle in 1.0 ml of methylene dichloride, 0.18 ml of 45% aqueous solution of fluoroboric acid was added under vigorous stirring. The agitation was continued for 5 min then Et2O (15 ml), the same amount of cold water, and 5-10 mg of ascorbic acid were added to the reaction flask. After vigorous shaking of the mixture the organic solution was separated, washed with cold water (5 15 ml), the solvent was removed and the residue was dried over CaCl2. 3-Ferrocenylmethylbenzo[d]thiazole-2(3H)-thione (5a) Yield 47%. Dark brown crystals, m.p. 134-135 °C. Anal.: С 59.27; Н 4.09; N 3.80; S 17.50%. Calc. for С18Н15FeNS2: С 59.18; Н 4.14; N 3.83; S 17.56%. EI/MS, m/z (RI%): 365 [M]+ (78). 1Н NMR (CDCl3, δ, ppm): 4.12 (s, 2H, Fc), 4.24 (s, 5H, Fc), 4.51 (s, 2H, Fc), 5.44 (s, 2H, CH2), 7.32-7.42 (m, 4H, Het). 13C NMR (CDCl3, δ, ppm): 45.5 (CH2), 68.4 (C5H4), 69.0 (C5H5), 69.9 (C5H4), 81.2 (ipso-C5H4), 112.8 (C-4, Het), 121.3 (C-7, Het), 124.7 (C-6, Het), 126.8 (C-5, Het), 127.6 (C-8, Het), 141.3 (C-9, Het), 189.1 (C=S).

Reference： [1]Rodionov, Alexey N.; Zherebker, Kira Ya.; Snegur, Lubov V.; Korlyukov, Alexander A.; Arhipov, Dmitry E.; Peregudov, Alexander S.; Ilyin, Mikhail M.; Nikitin, Oleg M.; Morozova, Nataliya B.; Simenel, Alexander A. [Journal of Organometallic Chemistry, 2015, vol. 783, p. 83 - 91]

42
[ 1273-86-5 ]
[ 220769-88-0 ]
ferrocenylmethyl 4,5-dichloroisothiazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In diethyl ether at 20 - 23℃; for 24h;	Synthesis of esters and diesters 14-22. General procedure: 1.1 mmol of triethylamine was added to a stirred mixture of 1.0 mmol of metallocene alcohol (7, 8, 12) or 0.45 mmol of ferrocene diol (10, 11) and 1.0 mmol of 4,5-dichloroisothiazole- or 5-arylisoxazole-3-carbonyl chloride in 50 mL of diethyl ether at 20-23°C. The reaction mixture was stirred at that temperature during 24 h. The precipitated triethylamine hydrochloride was filtered off and washed with diethyl ether (5 × 10 mL). The filtrate was washed with 10 % aqueous NaCl and 5 % aqueous NaHCO3. The solvent was removed, and the residue was recrystallized from a benzene-hexane (2 : 1) mixture (14, 15, 19, and 20) or from hexane (16,17, 21, and 22). 3,4,4-Trichloro-1-cymantrenylbut-3-en-1-yl 4,5-dichloroisothiazole-3-carboxylate 18 was obtained as a viscous oil and was used without further purification.

Reference： [1]Potkin; Dikusar; Kletskov; Petkevich; Semenova; Kolesnik; Zvereva; Zhukovskaya; Rosentsveig; Levkovskaya; Zolotar [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 338 - 343][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 338 - 343,6]

43
[ 78189-50-1 ]
[ 1273-86-5 ]
ferrocenylmethyl 5-phenylisoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In diethyl ether at 20 - 23℃; for 24h;	Synthesis of esters and diesters 14-22. General procedure: 1.1 mmol of triethylamine was added to a stirred mixture of 1.0 mmol of metallocene alcohol (7, 8, 12) or 0.45 mmol of ferrocene diol (10, 11) and 1.0 mmol of 4,5-dichloroisothiazole- or 5-arylisoxazole-3-carbonyl chloride in 50 mL of diethyl ether at 20-23°C. The reaction mixture was stirred at that temperature during 24 h. The precipitated triethylamine hydrochloride was filtered off and washed with diethyl ether (5 × 10 mL). The filtrate was washed with 10 % aqueous NaCl and 5 % aqueous NaHCO3. The solvent was removed, and the residue was recrystallized from a benzene-hexane (2 : 1) mixture (14, 15, 19, and 20) or from hexane (16,17, 21, and 22). 3,4,4-Trichloro-1-cymantrenylbut-3-en-1-yl 4,5-dichloroisothiazole-3-carboxylate 18 was obtained as a viscous oil and was used without further purification.

Reference： [1]Potkin; Dikusar; Kletskov; Petkevich; Semenova; Kolesnik; Zvereva; Zhukovskaya; Rosentsveig; Levkovskaya; Zolotar [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 338 - 343][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 338 - 343,6]

44
[ 1273-86-5 ]
[ 88958-29-6 ]
ferrocenylmethyl 5-(4-methylphenyl)isoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In diethyl ether at 20 - 23℃; for 24h;	Synthesis of esters and diesters 14-22. General procedure: 1.1 mmol of triethylamine was added to a stirred mixture of 1.0 mmol of metallocene alcohol (7, 8, 12) or 0.45 mmol of ferrocene diol (10, 11) and 1.0 mmol of 4,5-dichloroisothiazole- or 5-arylisoxazole-3-carbonyl chloride in 50 mL of diethyl ether at 20-23°C. The reaction mixture was stirred at that temperature during 24 h. The precipitated triethylamine hydrochloride was filtered off and washed with diethyl ether (5 × 10 mL). The filtrate was washed with 10 % aqueous NaCl and 5 % aqueous NaHCO3. The solvent was removed, and the residue was recrystallized from a benzene-hexane (2 : 1) mixture (14, 15, 19, and 20) or from hexane (16,17, 21, and 22). 3,4,4-Trichloro-1-cymantrenylbut-3-en-1-yl 4,5-dichloroisothiazole-3-carboxylate 18 was obtained as a viscous oil and was used without further purification.

Reference： [1]Potkin; Dikusar; Kletskov; Petkevich; Semenova; Kolesnik; Zvereva; Zhukovskaya; Rosentsveig; Levkovskaya; Zolotar [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 338 - 343][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 338 - 343,6]

45
[ 108-77-0 ]
[ 1273-86-5 ]
C₃₆H₃₃Fe₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 1,3,5-trichloro-2,4,6-triazine; 1-ferrocenylmethanol In tetrahydrofuran for 0.5h; Cooling with ice; Stage #2: With dmap In tetrahydrofuran for 8.5h; Reflux;	2.2. The Procedure for the Preparation of the Target Compound 1 Cyanuric chloride (TCT)(0.184g, 1mmol) was added intoa 50mL one-necked round-bottom flask with 10mL dry THF.The mixture was stirred in a cold bath and ferrocenemethanol(0.864g, 4mmol) in 10mL dry THF was slowly added tothe reaction system using a syringe. The mixture was stirred in the cold bath for 30min. Subsequently, DMAP (0.366g,3mmol) in 10mL dry THF was also slowly added to the reactionsystem using a syringe. The mixture was stirred in thecold bath for an additional 30min. Then, the temperature naturally rose to room temperature and was stirred for 8h.This time, the reaction system was refluxed. After the completion of the reaction indicated by simple TLC analysis, the solvent was evaporated under the reduced pressure, and theresidual was directly purified by column chromatography(EtOAc/Petroleum ether: 5:12:1) to obtain the target compound 1. 0.506g, light yellow solid, yield, 70%, Mp.:199-201 oC, 1H NMR(400MHz, CDCl3) (ppm): 4.73(s, 6H,32H of C5H4), 4.38(s, 6H, 32H of C5H4), 4.15(s, 15H,3C5H5), 4.10(s, 6H, 3CH2); 13C NMR(100MHz, CDCl3) (ppm): 148.7(3C=N), 81.5(6C), 70.4(6C), 68.7(15C),68.5(3C), 42.1(3CH2); ESI-MS(m/e, 100%) 746([M+23]+,100); Anal.calcd. for C36H33N3O3Fe3: N, 5.81; C, 59.75; H,4.56; Found: N, 5.75; C, 59.57 ; H, 4.64
70%	With dmap In tetrahydrofuran at 0℃; Reflux;	1 Example 1 Synthesis of ferrocene derivative containing nitrogen free radicals The cyanuric chloride (TCT)(0.184 g, 1 mmol) and 30 mL of dry tetrahydrofuran were added to a 100 mL round bottom flask,To a stirred solution of 20 mL of ferrocene methanol (0.864 g, 4 mmol) Of the dry tetrahydrofuran solution was slowly added dropwise to the reaction system.After stirring for 30 minutes under ice bath, 10 mL of a solution containing DMAP (0.366 g, 3 mmol)In a dry tetrahydrofuran solution was slowly added dropwise to the reaction system, and the mixture was stirred at room temperature for 5 minutes after stirring for 30 minutes. After the reaction was carried out at room temperature for 5 to 6 hours, the reaction was refluxed. After completion of the reaction, the reaction solution was concentrated under reduced pressure,The residue was separated by column chromatography using (V petroleum ether: V ethyl acetate, 5: 1-2: 1)The mobile phase was eluted to give nitroxyl radical containing ferrocene derivative I, 0.506 g, yield: 70%.

Reference： [1]Yong, Jianping; Wu, Xiaoyuan; Liao, Jianzhen; Lu, Canzhong; Liu, Xiaolong [Medicinal Chemistry, 2016, vol. 12, # 5, p. 426 - 431]
[2]Current Patent Assignee: XIANMEN INST OF RARE EARTH MATERIALS - CN104804047, 2017, B Location in patent: Paragraph 0047-0048

46
[ 288-88-0 ]
(vinyloxy)methylferrocene [ No CAS ]
[ 1273-86-5 ]
[ 713108-31-7 ]
1,1-bis(ferrocenylmethoxy)ethane [ No CAS ]
1-[1-(ferrocenylmethoxy)ethyl]-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 22% 3: 12% 4: 10%	With trifluoroacetic acid In 1,2-dimethoxyethane at 45℃; for 2h;	12 4.3.7 Reaction of vinyloxymethylferrocene with 1,2,4-triazole A mixture of vinyloxymethylferrocene (242 mg, 1 mmol), 1,2,4-triazole (69 mg, 1 mmol) and CF3CO2H (6 mg, 5 mol %) in dry DME (2 mL) was stirred at 45° for 2 h. After removal of the volatiles, the residue was separated by column chromatography (Al2O3, 1.5×10 cm) using hexane/Et2O (1:1, v/v), then Et2O as the eluent to afford acetal 4 (27 mg, yield 12%), products 10 and 11, and ferrocenylmethanol (21 mg, 10 %).

Reference： [1]Oparina, Ludmila A.; Artem'ev, Alexander V.; Vysotskaya, Oksana V.; Tarasova, Olga A.; Shagun, Vladimir A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A. [Tetrahedron, 2016, vol. 72, # 29, p. 4414 - 4422]

47
[ 1273-86-5 ]
[ 98-86-2 ]
3-ferrocen-2-yl-1-phenylpropan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With dimanganese decacarbonyl; sodium hydroxide In toluene at 110℃; for 2h; Inert atmosphere; Glovebox; Sealed tube;
92%	With C₃₈H₃₆Cl₄Ir₂N₄; caesium carbonate In tert-Amyl alcohol for 12h; Reflux;	14 Example 14: 3-ferrocen-2-yl-1-phenylpropan-1-one Acetophenone (60 mg, 0.5 mmol),Cat. [Ir] (5.4 mg, 0.005 mmol, 1.0 mol%),Cesium carbonate (33 mg, 0.1 mmol, 0.2 equiv.),Ferrocene methanol (130 mg, 0.6 mmol)And tert-amyl alcohol (1 ml) were successively added to a 5 mL round bottom flask.The reaction mixture was refluxed in air for 12 hours,Cool to room temperature.Rotate the solvent to remove the solvent,The purified title compound was then purified by column chromatography (developing solvent: petroleum ether / ethyl acetate)Yield: 92%
92%	With C₃₈H₃₇Cl₂N₃O₄Pd; potassium hydroxide In toluene at 115℃; for 6h;

87%	With bis(μ-chloro)-bis[1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C(2'),N-iridium chloride]; caesium carbonate In tert-Amyl alcohol for 12h; Reflux;
82%	With C₁₆H₁₄IrN₂O₃; caesium carbonate In tert-Amyl alcohol for 6h; Reflux;	14 3-Ferrocenyl-1-phenylpropan-1-one Acetophenone (120mg, 1mmol), cat.1 (5.4mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol,0.1equiv.), Ferrocene methanol (238mg, 1.1mmol) and tert-amyl alcohol (1ml) were sequentially added to 5mL round bottom flask.After the reaction mixture was refluxed in air for six hours, cooled to room temperature. The solvent is removed by rotary evaporation, then purified by column chromatography (developingOpen solvent: petroleum ether / ethyl acetate) to give pure target compound, yield: 82%
80%	With [(Cp*IrCl)₂(4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine)][Cl]₂; potassium hydroxide In water at 100℃; for 12h; Green chemistry;
80%	With [(Cp*IrCl)2(thbpym)][Cl]2; potassium hydroxide In water for 12h; Reflux;	15 Example 15: 3-(Ferrocenyl)-1-phenyl-1-acetone Ferrocene methanol(108mg, 0.5mmol), acetophenone (78.1mg, 0.65mmol), [(Cp*IrCl)2(thbpym)][Cl]2 (2.5mg, 0.0025mmol, 1mol Ir%), potassium hydroxide (28mg , 0.5mmol, 1equiv), and water (1mL) were sequentially added to a 5mL round bottom flask. After the reaction mixture was refluxed in air for 12 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate), yield: 80%.

Reference： [1]Lan, Xiao-Bing; Ye, Zongren; Huang, Ming; Liu, Jiahao; Liu, Yan; Ke, Zhuofeng [Organic Letters, 2019, vol. 21, # 19, p. 8065 - 8070]
[2]Current Patent Assignee: NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106478395, 2017, A Location in patent: Paragraph 0090; 0091; 0092; 0093; 0094
[3]Çetinkaya, Bekir; Eroğlu, Zafer; Gülcemal, Süleyman; Metin, Önder; Ovezova, Mamajan [Dalton Transactions, 2021, vol. 50, # 31, p. 10896 - 10908]
[4]Liu, Pengcheng; Liang, Ran; Lu, Lei; Yu, Zhentao; Li, Feng [Journal of Organic Chemistry, 2017, vol. 82, # 4, p. 1943 - 1950]
[5]Current Patent Assignee: NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105439787, 2016, A Location in patent: Paragraph 0090; 0091; 0092; 0093; 0094
[6]Meng, Chong; Xu, Jing; Tang, Yawen; Ai, Yao; Li, Feng [New Journal of Chemistry, 2019, vol. 43, # 35, p. 14057 - 14065]
[7]Current Patent Assignee: NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN111499503, 2020, A Location in patent: Paragraph 0092-0096

48
[ 1273-86-5 ]
[ 51826-90-5 ]
C₁₇H₂₆FeO₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diethylaminomethyl-polystyrene In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	7 Synthesis of an Ether-Linked Ferrocene Silane Example 7 Synthesis of an Ether-Linked Ferrocene Silane This example and the following Examples 8 and 9 describe compounds and methods of the invention for making an AIM-amide-linked sol-gel matrix and corresponding AIE of the invention. Hydroxymethyl ferrocene was reacted with (3-bromopropyl)trimethoxysilane to obtain the silane precursor, as shown in the following reaction scheme:

Reference： [1]Current Patent Assignee: PARKER-HANNIFIN CORP - US9417204, 2016, B2 Location in patent: Page/Page column 29

49
[ 1273-86-5 ]
[ 536-74-3 ]
[ 51831-56-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With C₅₅H₄₃ClIrNP₂; sodium hydroxide In 1,4-dioxane at 110℃; for 36h; Schlenk technique; Inert atmosphere;	19 example 19 Synthesis of 1-ferrocenyl-3-phenyl-1-propanone To a 10 ml Schlek reaction tube under a high-purity nitrogen atmosphere was added 0.20 mmol of benzoquinoline triphenylphosphine iridium hydrogen (16), lmmol of phenylacetylene, 2.3 mmol of ferrocene methanol, 0.8 mmol of sodium hydroxide and 3 ml of dioxane were charged. The reaction tube was replaced with nitrogen three times and then heated to 110 ° C with an oil bath under magnetic stirring. The reaction was refluxed for 36 hours. The filtrate was concentrated using a rotary evaporator and the remaining residue was purified by chromatography on oil (100 mL). The residue was purified by flash chromatography on silica gel eluting with an oil bath and the bath was cooled to room temperature. Ether as eluent, and separated by silica gel thin layer chromatography to obtain pure product 1-ferrocenyl-3-phenyl-1-propanone in a yield of 96%.

Reference： [1]Current Patent Assignee: LUOYANG NORMAL UNIVERSITY - CN103242372, 2016, B Location in patent: Paragraph 0059; 0060

50
[ 1273-86-5 ]
[ 541-41-3 ]
hydroxymethylferrocene ethyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-ferrocenylmethanol With n-butyllithium In diethyl ether; hexane for 0.0833333h; Inert atmosphere; Stage #2: chloroformic acid ethyl ester In diethyl ether; hexane at 20℃; Inert atmosphere; Stage #3: In diethyl ether; hexane at 20℃; Inert atmosphere;	4.2 General procedure for generation of carbonates 1a-c. decomposition of carbonates 1a-c General procedure: A solution of n-BuLi (1 eq.) in hexane was added dropwise to a solution of FcCH(R)OH (150mg) and 7 (0.083 eq.) in diethyl ether (10ml). The mixture was stirred for 5min and EtOC(O)Cl was added followed by 5min stirring extra. [If necessary, the solvent may be changed at the moment by removing diethyl ether at 20°C under vacuum to dryness followed by a re-dissolution of the residue in another solvent (10ml)]. The resulting mixture was allowed to stir at 20°C. Periodically, aliquots of the reaction mixture (1.0ml) were taken. Each aliquot was quenched with water (1.0ml) and the products were extracted with diethyl ether (2ml). The organic solution was dried over Na2SO4 and the solvent was evaporated at reduced pressure. The content of ethers 8a-c in the probes was monitored with 1H NMR spectra by a comparison of the integral intensities of the peaks of ether 8 with that ones of the reference compound 7. The decomposition of a carbonate was considered complete when the ratio of the peak intensities mentioned above rested unchanged in the next aliquot (see Fig.1).

Reference： [1]Shevaldina, Ekaterina V.; Shagina, Anastasia D.; Kalinin, Valery N.; Ponomaryov, Andrey B.; Smol'yakov, Alexandr F.; Moiseev, Sergey K. [Journal of Organometallic Chemistry, 2017, vol. 836-837, p. 1 - 7]

51
[ 1273-86-5 ]
3⁽⁵⁾-(ferrocen-1-yl)pyrazole [ No CAS ]
1-(ferrocenylmethyl)-3-ferrocenyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrafluoroboric acid In dichloromethane; water regioselective reaction;	General procedure for alkylationof ferrocenylpyrazoles General procedure: To a mixture of 1.0 mmol ferrocenyl alcohol and 1.0 mmolof the corresponding pyrazoles in 1 cm3 of methylenechloride, 0.18 cm3 of 48% aqueous fluoroboric acid(1.0 mmol) was added with vigorous stirring. Stirring wascontinued for 5-10 min after which 10 cm3 of water and10 cm3 of diethyl ether were added. The resulting mixturewas washed with water (2 9 15 cm3) and the organic layerwas separated and dried over CaCl2. The solvent wasremoved in vacuo.1-(Ferrocenylmethyl)-3-ferrocenyl-1H-pyrazole(4a, C24H22Fe2N2)Yield 67%; bronze oil; 1H NMR (400 MHz, CDCl3):d = 7.26 (d, J = 2 Hz, 1H, Pz), 6.27 (d, J = 2 Hz, 1H,Pz), 5.07 (s, 2H, CH2), 4.70 (s, 2H, Fc), 4.30 (s, 2H, Fc),4.27 (s, 2H, Fc), 4.20 (m, 7H, Fc), 4.09 (s, 5H, Fc) ppm;13C NMR (100 MHz, CDCl3): d = 148.8, 128.2, 103.3,84.3, 79.4, 69.4, 68.9, 68.3, 68.2, 68.0, 66.5, 48.6 ppm; MS(70 eV): m/z = 450 (M?, 100).

Reference： [1]Rodionov, Alexey N.; Gerasimova, Maria D.; Osipova, Elena Yu.; Korlyukov, Alexander A.; Peregudov, Alexander S.; Simenel, Alexander A. [Monatshefte fur Chemie, 2017, vol. 148, # 5, p. 925 - 932]

52
[ 1273-86-5 ]
[ 1290545-93-5 ]
1-(ferrocenylmethyl)-5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrafluoroboric acid In dichloromethane; water regioselective reaction;	General procedure for alkylationof ferrocenylpyrazoles General procedure: To a mixture of 1.0 mmol ferrocenyl alcohol and 1.0 mmolof the corresponding pyrazoles in 1 cm3 of methylenechloride, 0.18 cm3 of 48% aqueous fluoroboric acid(1.0 mmol) was added with vigorous stirring. Stirring wascontinued for 5-10 min after which 10 cm3 of water and10 cm3 of diethyl ether were added. The resulting mixturewas washed with water (2 9 15 cm3) and the organic layerwas separated and dried over CaCl2. The solvent wasremoved in vacuo.

Reference： [1]Rodionov, Alexey N.; Gerasimova, Maria D.; Osipova, Elena Yu.; Korlyukov, Alexander A.; Peregudov, Alexander S.; Simenel, Alexander A. [Monatshefte fur Chemie, 2017, vol. 148, # 5, p. 925 - 932]

53
[ 1273-86-5 ]
3⁽⁵⁾-ferrocenyl-5⁽³⁾-methylpyrazol [ No CAS ]
5-methyl-1-(ferrocenylmethyl)-3-ferrocenyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrafluoroboric acid In dichloromethane; water regioselective reaction;	General procedure for alkylationof ferrocenylpyrazoles General procedure: To a mixture of 1.0 mmol ferrocenyl alcohol and 1.0 mmolof the corresponding pyrazoles in 1 cm3 of methylenechloride, 0.18 cm3 of 48% aqueous fluoroboric acid(1.0 mmol) was added with vigorous stirring. Stirring wascontinued for 5-10 min after which 10 cm3 of water and10 cm3 of diethyl ether were added. The resulting mixturewas washed with water (2 9 15 cm3) and the organic layerwas separated and dried over CaCl2. The solvent wasremoved in vacuo.1-(Ferrocenylmethyl)-3-ferrocenyl-1H-pyrazole(4a, C24H22Fe2N2)Yield 67%; bronze oil; 1H NMR (400 MHz, CDCl3):d = 7.26 (d, J = 2 Hz, 1H, Pz), 6.27 (d, J = 2 Hz, 1H,Pz), 5.07 (s, 2H, CH2), 4.70 (s, 2H, Fc), 4.30 (s, 2H, Fc),4.27 (s, 2H, Fc), 4.20 (m, 7H, Fc), 4.09 (s, 5H, Fc) ppm;13C NMR (100 MHz, CDCl3): d = 148.8, 128.2, 103.3,84.3, 79.4, 69.4, 68.9, 68.3, 68.2, 68.0, 66.5, 48.6 ppm; MS(70 eV): m/z = 450 (M?, 100).

Reference： [1]Rodionov, Alexey N.; Gerasimova, Maria D.; Osipova, Elena Yu.; Korlyukov, Alexander A.; Peregudov, Alexander S.; Simenel, Alexander A. [Monatshefte fur Chemie, 2017, vol. 148, # 5, p. 925 - 932]

54
[ 1273-86-5 ]
[ 1271-42-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With di-isopropyl azodicarboxylate; all-trans-retinoic-acid; triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere;	1 Synthesis and purification of ferrocene carboxylic acid Ferrocene methanol (ferrocenyl methanol, 3mmol), triphenylphosphine (PPh3,1.18g, 4.5mmol), all-trans retinoic acid (ATRA, 3mmol), was dissolved in 20mL of tetrahydrofuran (THF), stir to dissolve, then under nitrogen, was added diisopropyl azodicarboxylate (DIAD, 0.8g, 4.5mmol) under conditions of 0 C . The reaction Thin chromatography (TLC) monitoring process, after the completion of the reaction continued at room temperature for 2 hours. 30 deg C and concentrated in vacuo by rotary evaporation to a thick oil, the product was extracted using silica gel column chromatography (ethyl acetate / petroleum ether = 2: 8 volume ratio) to give the product as the first ferrocene carboxylic acid (FCRA ), 83% yield
78%	With oxygen at 120℃; for 16h; Green chemistry;
77%	With potassium hydroxide In toluene at 120℃; for 24h;	2.3 General procedure for the dehydrogenation of benzylic alcohols General procedure: Benzylic alcohols (1.0mmol), solid 1a (0.2-2mol %), KOH (2-4 equiv.) and 1.5mL toluene were charged sequentially in a 25mL tube with a magnetic bar. The reaction tube was stirred at 120°C for 12-48h attached with an open bubbler. After the certain reaction time, water (5mL) was added, and the mixture was extracted with diethyl ether (3×5mL). Then the aqueous phase was acidified with HCl (6M) and further extracted with ethyl acetate (3×10mL). The combined ethyl acetate solution was washed with brine (15mL), dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure, the pure acids was obtained and weighted for calculating the yield.

Reference： [1]Current Patent Assignee: JILIN UNIVERSITY - CN106265600, 2017, A Location in patent: Paragraph 0021-0023
[2]Liu, Kai-Jian; Jiang, Si; Lu, Ling-Hui; Tang, Ling-Li; Tang, Shan-Shan; Tang, Hai-Shan; Tang, Zilong; He, Wei-Min; Xu, Xinhua [Green Chemistry, 2018, vol. 20, # 13, p. 3038 - 3043]
[3]Yin, Shenxiang; Zheng, Qingshu; Chen, Jie; Tu, Tao [Journal of Catalysis, 2022, vol. 408, p. 165 - 172]

55
[ 1273-86-5 ]
[ 2382-96-9 ]
3-(ferrocenylmethyl)benz[d]oxazole-2-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrafluoroboric acid In dichloromethane; water at 20℃; regioselective reaction;	Synthesis of ferrocenylalkyl-2-mercaptobenzoxazoles (general procedure). General procedure: A 48% aqueous solution of tetrafluoroboric acid (0.21 mL, 1.2 mmol) was added to a suspension of ferrocenyl carbinol (1 mmol) and 2mercaptobenzoxazole (1 mmol) in dichloromethane (1 mL) under vigorous stirring. The stirring was continued for 5-15 mL. Then water (10 mL) and diethyl ether (10 mL) were added to the reaction mixture. The resulting mixture was washed with water (2×20 mL), the organic layer was separated and dried with Na2SO4. The solvent was removed under water pump vacuum. 3(Ferrocenylmethyl)benz[d]oxazole-2-thione (1a). Yield 72%. Yellow powder. M.p. 166.8-167.2 °C. Found (%): C, 61.97; H, 4.32; N, 4.04; Fe, 15.96. Calculated (%): C, 61.91; H, 4.33; N, N, 4.01; Fe, 15.99. Rf 0.6 (petroleum ether-ethyl acetate, 3 : 1). MS, m/z (Irel(%)): 349 [M]+ (100). 1H NMR, δ: 4.18 (s, 2 H, C5H4); 4.27 (s, 5 H, C5H5); 4.48 (s, 2 H, C5H4); 5.21 (s, 2 H, CH2); 7.15 (d, 1 H, Het, J = 7.6 Hz); 7.22-7.31 (m, 2 H, Het); 7.32 (d, 1 H, Het, J = 7.6 Hz). 13C NMR, δ: 45.66 (CH2), 68.74 (C5H4), 68.96 (C5H5), 69.69 (C5H4), 80.29 (ipsoC5H4), 109.81 (Het), 110.34 (Het), 124.17 (Het), 124.75 (Het), 131.51 (Het), 147.05 (Het), 180.06 (C=S).

Reference： [1]Osipova, E. Yu.; Ivanova; Rodionov; Korlyukov; Arkhipov; Simenel [Russian Chemical Bulletin, 2016, vol. 65, # 12, p. 2868 - 2872][Izv. Akad. Nauk, Ser. Khim., 2016, vol. 65, # 12, p. 2868 - 2872,5]

56
[ 1273-86-5 ]
C₂H₁₃B₁₀S [ No CAS ]
[(m-Carboran-9-yl)thio]ferrocenyl methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonium cerium (IV) nitrate In nitromethane at 20℃; Inert atmosphere;	2.3. General procedure for the reactions of ferrocenyl alcohols 1, 2 withmercaptocarboranes 3, 4 and thioglycolic acid General procedure: To a solution of ferrocenyl alcohol 1 or 2 (2.0 mmol) and correspondingmercapto derivative in dry MeNO2 (5 mL) CAN (22 mg,0.04 mmol, 0.2 mol%) was added. The resulting mixture was stirredat room temperature until TLC analysis revealed complete disappearanceof starting alcohol 1 or 2 (usually 3-4 h). Then reactionmixture was poured onto a water (40 mL), organic layer was separated,the aqueous phase was extracted with EtOAc (2 10 mL),and the combined organic solution was dried over Na2SO4, filteredand the solvents were evaporated in vacuo. The remained productwas treated with CH2Cl2 (50 ml) and passed through a silica gellayer (2.5 cm) on the filter to give corresponding products 5-9,11 after the evaporation of volatiles at reduced pressure.