Alternatived Products of [ 17873-01-7 ]
Product Details of [ 17873-01-7 ]
CAS No. : | 17873-01-7 |
MDL No. : | MFCD00048020 |
Formula : |
C10H16O3Si
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | XQEGZYAXBCFSBS-UHFFFAOYSA-N |
M.W : |
212.32
|
Pubchem ID : | 2760672 |
Synonyms : |
|
Application In Synthesis of [ 17873-01-7 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 17873-01-7 ]
- 1
-
[ 14371-10-9 ]
-
[ 17873-01-7 ]
-
[ 92804-29-0 ]
Yield | Reaction Conditions | Operation in experiment |
85% |
With tetrabutyl ammonium fluoride; antimony(III) chloride; acetic acid In acetonitrile at 60℃; for 24h; |
|
- 2
-
[ 5153-67-3 ]
-
[ 17873-01-7 ]
-
[ 1882-47-9 ]
Yield | Reaction Conditions | Operation in experiment |
54% |
With tetrabutyl ammonium fluoride; antimony(III) chloride; acetic acid In acetonitrile at 60℃; for 24h; |
|
- 3
-
(E)-1-phenyl-2-buten-1-one
[ No CAS ]
-
[ 17873-01-7 ]
-
[ 62557-95-3 ]
Yield | Reaction Conditions | Operation in experiment |
47% |
With tetrabutyl ammonium fluoride; antimony(III) chloride; acetic acid In acetonitrile at 60℃; for 34h; |
|
- 4
-
[ 18402-83-0 ]
-
[ 17873-01-7 ]
-
[ 182482-48-0 ]
Yield | Reaction Conditions | Operation in experiment |
81% |
In 1,4-dioxane; water at 95℃; for 23h; |
|
- 5
-
[ 626-55-1 ]
-
[ 17873-01-7 ]
-
[ 4423-09-0 ]
Yield | Reaction Conditions | Operation in experiment |
92% |
With sodium hydroxide at 135℃; for 24h; |
|
81% |
With sodium hydroxide at 60℃; for 9h; |
|
71% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube; |
|
71% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation; |
|
Reference:
[1]Wolf, Christian; Lerebours, Rachel
[Organic Letters, 2004, vol. 6, # 7, p. 1147 - 1150]
[2]Shi, Shengyin; Zhang, Yuhong
[Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5927 - 5930]
[3]Martinez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
[4]Martínez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
- 6
-
[ 108-86-1 ]
-
[ 17873-01-7 ]
-
[ 644-08-6 ]
Yield | Reaction Conditions | Operation in experiment |
96% |
With N-methyliminodiacetic acid; sodium fluoride; potassium hydroxide; palladium dichloride In water; isopropyl alcohol at 80℃; for 6h; |
|
86% |
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 4h; |
|
73% |
With sodium hydroxide at 60℃; for 8h; |
|
68 %Spectr. |
With tetrabutyl-ammonium chloride; sodium hydroxide In water at 80℃; for 3h; |
General Procedure for Hiyama Coupling Reaction (Table 1)
General procedure: To a screw-capped vial with a stirring bar were added 4-bromotoluene(86.4 mg, 0.5 mmol), phenyltrimethoxysilane (152 mg,0.75 mmol), PS-PdONPs (2.9 mg, 1.5 mol% of Pd), TBAC (142 mg,0.5 mmol), and aq NaOH solution (1.5 M, 1 mL). After stirring at80 °C for 3 h, the reaction mixture was cooled to r.t. by immediatelyimmersing the vial in H2O (ca. 20 °C) for about 10 min.After separating the catalyst and the aqueous phase by centrifugation,the aqueous phase was decanted. The recovered catalystwas washed with H2O (5 × 3.0 mL) and Et2O (5 × 3.0 mL), whichwere then added to the aqueous phase. The aqueous phase wasextracted eight times with Et2O. The combined organic extractswere dried over MgSO4 and concentrated under reduced pressure.The product was analyzed by 1H NMR. The recovered catalystwas dried in vacuo and reused. Furthermore, the amount ofPd metal in the aqueous phase determined by ICP-AES analysiswas <0.1 ppm. |
Reference:
[1]Guo, Mengping; Qi, Liang; Zhang, Qiaochu; Zhu, Zhiyong; Li, Wei; Li, Xiaogang
[Organic and Biomolecular Chemistry, 2014, vol. 12, # 36, p. 7136 - 7139]
[2]Li, Jin-Heng; Deng, Chen-Liang; Liu, Wen-Jie; Xie, Ye-Xiang
[Synthesis, 2005, # 18, p. 3039 - 3044]
[3]Shi, Shengyin; Zhang, Yuhong
[Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5927 - 5930]
[4]Ohtaka, Atsushi; Kotera, Takamasa; Sakon, Akira; Ueda, Kouhei; Hamasaka, Go; Uozumi, Yasuhiro; Shinagawa, Tsutomu; Shimomura, Osamu; Nomura, Ryôki
[Synlett, 2016, vol. 27, # 8, p. 1202 - 1206]
- 7
-
[ 104-92-7 ]
-
[ 17873-01-7 ]
-
[ 53040-92-9 ]
Yield | Reaction Conditions | Operation in experiment |
83% |
With tetrabutyl ammonium fluoride; tris-(o-tolyl)phosphine at 80℃; for 0.75h; |
|
78% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube; |
|
78% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation; |
|
70% |
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 4h; |
|
62% |
With N-methyliminodiacetic acid; sodium fluoride; potassium hydroxide; palladium dichloride In water; isopropyl alcohol at 80℃; for 12h; |
|
Reference:
[1]Li, Jin-Heng; Deng, Chen-Liang; Xie, Ye-Xiang
[Synthesis, 2006, # 6, p. 969 - 974]
[2]Martinez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
[3]Martínez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
[4]Li, Jin-Heng; Deng, Chen-Liang; Liu, Wen-Jie; Xie, Ye-Xiang
[Synthesis, 2005, # 18, p. 3039 - 3044]
[5]Guo, Mengping; Qi, Liang; Zhang, Qiaochu; Zhu, Zhiyong; Li, Wei; Li, Xiaogang
[Organic and Biomolecular Chemistry, 2014, vol. 12, # 36, p. 7136 - 7139]
- 8
-
[ 106-38-7 ]
-
[ 17873-01-7 ]
-
[ 613-33-2 ]
Reference:
[1]Journal of Organic Chemistry,2007,vol. 72,p. 5927 - 5930
[2]Asian Journal of Chemistry,2014,vol. 26,p. 1015 - 1018
[3]Synthesis,2005,p. 3039 - 3044
[4]Synthesis,2006,p. 969 - 974
[5]Organic and Biomolecular Chemistry,2014,vol. 12,p. 7136 - 7139
- 9
-
[ 17873-01-7 ]
-
[ 100-00-5 ]
-
[ 2143-88-6 ]
Yield | Reaction Conditions | Operation in experiment |
98% |
With tetrabutyl ammonium fluoride; tris-(o-tolyl)phosphine at 80℃; for 0.666667h; |
|
88% |
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 12h; |
|
84% |
With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; |
2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes
General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4. |
Reference:
[1]Li, Jin-Heng; Deng, Chen-Liang; Xie, Ye-Xiang
[Synthesis, 2006, # 6, p. 969 - 974]
[2]Li, Jin-Heng; Deng, Chen-Liang; Liu, Wen-Jie; Xie, Ye-Xiang
[Synthesis, 2005, # 18, p. 3039 - 3044]
[3]Location in patent: experimental part
Gu, Zheng-Song; Shao, Li-Xiong; Lu, Jian-Mei
[Journal of Organometallic Chemistry, 2012, vol. 700, p. 132 - 134]
- 10
-
[ 17873-01-7 ]
-
[ 586-78-7 ]
-
[ 2143-88-6 ]
Yield | Reaction Conditions | Operation in experiment |
95% |
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 4h; |
|
90% |
With sodium hydroxide at 60℃; for 2h; |
|
Reference:
[1]Li, Jin-Heng; Deng, Chen-Liang; Liu, Wen-Jie; Xie, Ye-Xiang
[Synthesis, 2005, # 18, p. 3039 - 3044]
[2]Shi, Shengyin; Zhang, Yuhong
[Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5927 - 5930]
- 11
-
[ 917086-20-5 ]
-
[ 17873-01-7 ]
-
(2R,7aS)-2-(4-Methyl-benzyl)-hexahydro-pyrrolizin-3-one
[ No CAS ]
-
(2S,7S)-2-(4-methylbenzyl)-hexahydropyrrolizin-3-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
76% |
In 1,4-dioxane; water at 110℃; for 24h; |
|
- 12
-
[ 930-68-7 ]
-
[ 17873-01-7 ]
-
[ 99495-15-5 ]
Yield | Reaction Conditions | Operation in experiment |
91% |
With tetrakis(actonitrile)copper(I) hexafluorophosphate; water at 120℃; for 4h; microwave irradiation; |
|
- 13
-
[ 51-17-2 ]
-
[ 17873-01-7 ]
-
[ 60057-83-2 ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h; |
|
- 14
-
[ 288-32-4 ]
-
[ 17873-01-7 ]
-
[ 25372-10-5 ]
Yield | Reaction Conditions | Operation in experiment |
58% |
With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h; |
|
- 15
-
[ 288-88-0 ]
-
[ 17873-01-7 ]
-
[ 2244-88-4 ]
Yield | Reaction Conditions | Operation in experiment |
96% |
With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h; |
|
- 16
-
[ 288-36-8 ]
-
[ 17873-01-7 ]
-
[ 20320-18-7 ]
Yield | Reaction Conditions | Operation in experiment |
57% |
With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h; |
|
- 17
-
6Pd(2+)*6(C5H4N)2*4C3N3(C5H4N)3*12NO3(1-)=Pd6((C5H4N)2)6(C3N3(C5H4N)3)4(NO3)12
[ No CAS ]
-
[ 17873-01-7 ]
-
6Pd(2+)*6C10N2H8*4C3N3(C5NH4)3*12NO3(1-)*(SiOOHC6H4CH3)3=(Pd(C5H4N)4)6(C3N3)4(NO3)12*(SiOOHC6H4CH3)3
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
90% |
In water silan suspended in aq. soln. of host at 100 °C, mixt. stirred for100 °C for 1 h; mixt. cooled to room temp., soln. filtered, evapd., product recrystd. from H2O; detnd. by XRD, NMR; |
|
- 18
-
[ 1016624-90-0 ]
-
[ 17873-01-7 ]
-
[ 1016627-44-3 ]
-
[ 1016627-28-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
With (1,2-dimethoxyethane)dichloronickel(II) In 1,4-dioxane at 20℃; for 16h; Title compound not separated from byproducts.; |
|
|
With (1,2-dimethoxyethane)dichloronickel(II) In 1,4-dioxane at 20℃; for 16h; Title compound not separated from byproducts.; |
|
Reference:
[1]Dai, Xing; Strotman, Neil A.; Fu, Gregory C.
[Journal of the American Chemical Society, 2008, vol. 130, # 11, p. 3302 - 3303]
[2]Dai, Xing; Strotman, Neil A.; Fu, Gregory C.
[Journal of the American Chemical Society, 2008, vol. 130, # 11, p. 3302 - 3303]
- 19
-
C17H19O4SN
[ No CAS ]
-
[ 17873-01-7 ]
-
4-(4'-methylbiphenyl-3-yl)morpholine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
81% |
With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere; |
|
- 20
-
[ 15161-04-3 ]
-
[ 17873-01-7 ]
-
[ 27331-34-6 ]
Yield | Reaction Conditions | Operation in experiment |
63% |
With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere; |
|
- 21
-
[ 7385-85-5 ]
-
[ 17873-01-7 ]
-
[ 59115-49-0 ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere; |
|
- 22
-
[ 17873-01-7 ]
-
[ 536-74-3 ]
-
[ 3287-02-3 ]
Yield | Reaction Conditions | Operation in experiment |
90% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; silver fluoride; sodium hydrogencarbonate In acetonitrile at 20℃; for 3h; |
|
Reference:
[1]Location in patent: scheme or table
Ye, Zhishi; Liu, Miaochang; Lin, Baoda; Wu, Huayue; Ding, Jinchang; Cheng, Jiang
[Tetrahedron Letters, 2009, vol. 50, # 5, p. 530 - 532]
- 23
-
[ 52843-75-1 ]
-
[ 17873-01-7 ]
-
[ 4423-09-0 ]
Yield | Reaction Conditions | Operation in experiment |
40% |
With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tetrahydrofuran; <i>tert</i>-butyl alcohol at 90℃; Inert atmosphere; |
|
- 24
-
[ 17873-01-7 ]
-
[ 52200-03-0 ]
-
[ 24423-07-2 ]
Yield | Reaction Conditions | Operation in experiment |
96% |
With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tetrahydrofuran; <i>tert</i>-butyl alcohol at 90℃; Inert atmosphere; |
|
- 25
-
[ 17873-01-7 ]
-
[ 59970-38-6 ]
-
1-(4-tert-butylphenyl)-4-methylbenzene
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
76% |
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; tetrabutyl ammonium fluoride; palladium diacetate; acetic acid In <i>tert</i>-butyl alcohol at 90℃; for 16h; Inert atmosphere; |
|
71% |
With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tetrahydrofuran; <i>tert</i>-butyl alcohol at 90℃; Inert atmosphere; |
|
Reference:
[1]So, Chau Ming; Lee, Hang Wai; Lau, Chak Po; Kwong, Fuk Yee
[Organic Letters, 2009, vol. 11, # 2, p. 317 - 320]
[2]Zhang, Liang; Qing, Jiang; Yang, Pengyuan; Wu, Jie
[Organic Letters, 2008, vol. 10, # 21, p. 4971 - 4974]
- 26
-
[ 1070731-22-4 ]
-
[ 17873-01-7 ]
-
[ 7383-87-1 ]
Yield | Reaction Conditions | Operation in experiment |
84% |
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; tetrabutyl ammonium fluoride; palladium diacetate; acetic acid In <i>tert</i>-butyl alcohol at 90℃; for 16h; Inert atmosphere; |
|
- 27
-
[ 10290-91-2 ]
-
[ 17873-01-7 ]
-
[ 59115-49-0 ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; tetrabutyl ammonium fluoride; palladium diacetate; acetic acid In <i>tert</i>-butyl alcohol at 90℃; for 16h; Inert atmosphere; |
|
- 28
-
[ 13141-42-9 ]
-
[ 17873-01-7 ]
-
C20H17N
[ No CAS ]
-
C20H17N
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 2-(2-phenylethynyl)pyridine; (4-methylphenyl)trimethoxysilane With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutyl ammonium fluoride; copper diacetate; triphenylphosphine In toluene at 20℃; for 2h;
Stage #2: With water In toluene at 110℃; for 12h; regioselective reaction; |
|
- 29
-
[ 1129-65-3 ]
-
[ 17873-01-7 ]
-
C19H22
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
88% |
Stage #1: (hex-1-yn-1-yl)benzene; (4-methylphenyl)trimethoxysilane With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutyl ammonium fluoride; copper diacetate; triphenylphosphine In toluene at 20℃; for 2h;
Stage #2: With water In toluene at 110℃; for 12h; regioselective reaction; |
|
- 30
-
[ 17873-01-7 ]
-
[ 501-65-5 ]
-
[ 70603-14-4 ]
Yield | Reaction Conditions | Operation in experiment |
80% |
Stage #1: (4-methylphenyl)trimethoxysilane; diphenyl acetylene With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutyl ammonium fluoride; copper diacetate; triphenylphosphine In toluene at 20℃; for 2h;
Stage #2: With water In toluene at 110℃; for 12h; |
|
- 31
-
5-chloro-1-(4-methoxybenzyl)-3-(phenylsulfanyl)pyrazin-2(1H)-one
[ No CAS ]
-
[ 17873-01-7 ]
-
5-chloro-3-(4-methylphenyl)-1-(4-methoxybenzyl)-2(1H)-pyrazinone
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
89% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; |
|
- 32
-
[ 17873-01-7 ]
-
[ 62-53-3 ]
-
[ 620-84-8 ]
Yield | Reaction Conditions | Operation in experiment |
65% |
Stage #1: (4-methylphenyl)trimethoxysilane With tetrabutyl ammonium fluoride; copper diacetate; tris(pentafluorophenyl)phosphine In dichloromethane; water at 20℃; for 0.0833333h; Molecular sieve;
Stage #2: aniline With oxygen In dichloromethane; water at 20℃; for 24h; |
|
Reference:
[1]Lin, Baoda; Liu, Miaochang; Ye, Zhishi; Ding, Jinchang; Wu, Huayue; Cheng, Jiang
[Organic and Biomolecular Chemistry, 2009, vol. 7, # 5, p. 869 - 873]
- 33
-
[ 109-09-1 ]
-
[ 17873-01-7 ]
-
[ 4467-06-5 ]
Yield | Reaction Conditions | Operation in experiment |
83% |
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 2h; Inert atmosphere; Neat (no solvent); |
|
- 34
-
[ 2398-37-0 ]
-
[ 17873-01-7 ]
-
[ 24423-07-2 ]
Yield | Reaction Conditions | Operation in experiment |
91% |
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 3h; Inert atmosphere; Neat (no solvent); |
|
- 35
-
[ 623-12-1 ]
-
[ 17873-01-7 ]
-
[ 53040-92-9 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 2h; Inert atmosphere; Neat (no solvent); |
|
82% |
With 3-(dicyclohexylphosphino)-2-(2-methoxyphenyl)-1-methyl-1-H-indole; tetrabutyl ammonium fluoride; palladium diacetate at 110℃; for 3h; Schlenk technique; Inert atmosphere; Sealed tube; |
|
Reference:
[1]Raders, Steven M.; Kingston, Jesudoss V.; Verkade, John G.
[Journal of Organic Chemistry, 2010, vol. 75, # 5, p. 1744 - 1747]
[2]Yuen, On Ying; So, Chau Ming; Man, Ho Wing; Kwong, Fuk Yee
[Chemistry - A European Journal, 2016, vol. 22, # 19, p. 6471 - 6476]
- 36
-
[ 98-81-7 ]
-
[ 17873-01-7 ]
-
[ 948-55-0 ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 1h; Inert atmosphere; Neat (no solvent); |
|
- 37
-
[ 586-77-6 ]
-
[ 17873-01-7 ]
-
[ 141082-00-0 ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate In 1,4-dioxane at 80℃; for 5h; Inert atmosphere; |
|
- 38
-
[ 603-76-9 ]
-
[ 17873-01-7 ]
-
[ 51358-08-8 ]
Yield | Reaction Conditions | Operation in experiment |
81% |
With tetrabutyl ammonium fluoride; palladium diacetate; acetic acid; silver(l) oxide In tetrahydrofuran; ethanol at 20℃; Inert atmosphere; regioselective reaction; |
|
- 39
-
[ 930-68-7 ]
-
[ 17873-01-7 ]
-
[ 6330-12-7 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With 1,10-Phenanthroline; palladium diacetate; silver fluoride In N,N-dimethyl-formamide at 60℃; |
|
Reference:
[1]Ye, Zhishi; Chen, Fan; Luo, Fang; Wang, Wenhui; Lin, Baoda; Jia, Xiaofei; Cheng, Jiang
[Synlett, 2009, # 13, p. 2198 - 2200]
- 40
-
[ 1008-89-5 ]
-
[ 17873-01-7 ]
-
2-[4’-methyl-(1,1’-biphenyl)-2-yl]pyridine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
63% |
With palladium diacetate; silver fluoride; p-benzoquinone In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; seal tube; |
|
67 %Chromat. |
With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In 1,2-dichloro-ethane at 140℃; for 20h; Inert atmosphere; |
|
Reference:
[1]Location in patent: experimental part
Li, Wu; Yin, Zhangwei; Jiang, Xiaoqing; Sun, Peipei
[Journal of Organic Chemistry, 2011, vol. 76, # 20, p. 8543 - 8548]
[2]Nareddy, Pradeep; Jordan, Frank; Szostak, Michal
[Organic and Biomolecular Chemistry, 2017, vol. 15, # 22, p. 4783 - 4788]
- 41
-
[ 17873-01-7 ]
-
[ 106-49-0 ]
-
[ 613-33-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
|
General procedure: The concentration of0.25mol aniline was dissolved in the mixture of 63 ml HCl and 63 ml water in600 ml beaker. After cooled to 0-5 oC with stirring, anilinehydrochloride crystallization. Aqueous solution of sodium nitrite (18gdissolved in 40 ml water) was added into beaker dropwise with stirring, keepingthe temperature under 5 oC. 40 g of sodium tetrafluoroboratesolution dissolved in 80 ml water was added to the diazonium salt solution, andthen continue to stir for 10 minutes. The solid was immediately washed by 10 ml5 % solution of sodium tetrafluoroborate for three times after filtered, andthen washed by 15 ml methanol twice to afford diazonium salt.A mixture of arenediazonium tetrafluoroborate salt(0.5 mmol), Pd(OAc)2 (5 mol%), TBAF (0.5 mmol) and aryl silanes (0.6mmol) was stirred in water (1 mL) at room termperature for 6 h. Afterwards, thereaction solution was filtered through a filter paper and the solution wasextracted by Et2O (1 mL) for three times. The organic phase wascombined and evaporated under reduced pressure. The residue was purified on aSiO2 column to afford the desired product. |
- 42
-
[ 141-32-2 ]
-
[ 17873-01-7 ]
-
[ 123248-21-5 ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With tetrabutyl ammonium fluoride; p-benzoquinone In tetrahydrofuran at 40℃; for 14h; |
|
60% |
With C14H16N6; palladium diacetate; silver fluoride In N,N-dimethyl acetamide at 60℃; for 24h; |
4.3. General procedure of palladium-catalyzed Mizoroki-Heck type reaction with aryl trialkoxysilanesCommentComment
General procedure: To a mixture of olefin (0.5 mmol), AgF (0.191 mg, 1.5 mmol), Pd(OAc)2 (5.6 mg, 25 μmol), and ligand 1e (6.7 mg, 25 μmol) in DMAc (1.0 mL) was added aryl trialkoxysilane (1.0 mmol) at room temperature under an atmosphere of air. The mixture was stirred at 60 °C. After 24 h, the mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane or hexane/EtOAc=100 to 10/1). |
Reference:
[1]Patra, Debabrata; Panja, Subir; Saha, Amit
[European Journal of Organic Chemistry, 2020, vol. 2020, # 7, p. 878 - 883]
[2]Location in patent: experimental part
Mino, Takashi; Shibuya, Masanori; Suzuki, Saori; Hirai, Kiminori; Sakamoto, Masami; Fujita, Tsutomu
[Tetrahedron, 2012, vol. 68, # 2, p. 429 - 432]
- 43
-
[ 17873-01-7 ]
-
[ 99-90-1 ]
-
[ 5748-38-9 ]
Yield | Reaction Conditions | Operation in experiment |
46% |
With 3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazolium chloride; water; palladium diacetate; sodium hydroxide at 120℃; for 1h; Microwave irradiation; |
|
- 44
-
[ 623-03-0 ]
-
[ 17873-01-7 ]
-
[ 50670-50-3 ]
Yield | Reaction Conditions | Operation in experiment |
81% |
With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; |
2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes
General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4. |
- 45
-
[ 1126-46-1 ]
-
[ 17873-01-7 ]
-
[ 49742-56-5 ]
Yield | Reaction Conditions | Operation in experiment |
79% |
With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; |
2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes
General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4. |
- 46
-
[ 17873-01-7 ]
-
[ 99-91-2 ]
-
[ 5748-38-9 ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; |
2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes
General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4. |
- 47
-
[ 624-31-7 ]
-
[ 17873-01-7 ]
-
[ 613-33-2 ]
Yield | Reaction Conditions | Operation in experiment |
80% |
With tetrabutyl ammonium fluoride; In water; toluene; at 100℃; for 20h; |
General procedure: Catalyst 1a22a (43 mg, 0.1 mol % of supported palladium) was added to a solution of aryl iodide (0.40 mmol, 1.0 equiv), aryltrialkoxysilane (0.80 mmol, 2.0 equiv), TBAF·3H2O (252 mg, 0.8 mmol, 2.0 equiv) in a mixture of toluene (5 mL) and H2O (50 muL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, 1a was filtered under vacuum on a 0.2 mum membrane. The catalyst was successively washed with toluene (10 mL) and Et2O (10 mL). The combined organic phases were washed with H2O (20 mL), dried with MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash-chromatography on silica gel. Catalyst 1a was dried under vacuum and can directly be used for another Hiyama coupling. |
- 48
-
AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)
[ No CAS ]
-
[ 17873-01-7 ]
-
[N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](4-tolyldimethoxysilanolate)gold(I)
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
99% |
With air In toluene at 20℃; for 1h; Inert atmosphere; |
|
- 49
-
AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)
[ No CAS ]
-
[ 17873-01-7 ]
-
(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(p-methylphenyl)gold
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
94% |
In 1,4-dioxane at 110℃; for 0.8h; Inert atmosphere; |
|
- 50
-
[ 17873-01-7 ]
-
[ 824-79-3 ]
-
[ 613-33-2 ]
- 51
-
[ 17873-01-7 ]
-
[ 613-33-2 ]
- 52
-
[ 3972-65-4 ]
-
[ 17873-01-7 ]
-
1-(4-tert-butylphenyl)-4-methylbenzene
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
80% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube; |
|
80% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation; |
|
Reference:
[1]Martinez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
[2]Martínez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
- 53
-
[ 95-46-5 ]
-
[ 17873-01-7 ]
-
[ 611-61-0 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube; |
|
82% |
With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation; |
|
Reference:
[1]Martinez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
[2]Martínez, Regina; Pastor, Isidro M.; Yus, Miguel
[European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 872 - 877]
- 54
-
[ 1483-82-5 ]
-
[ 17873-01-7 ]
-
[ 3287-02-3 ]
Yield | Reaction Conditions | Operation in experiment |
90% |
With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; |
Synthesis of internal alkynes (3-12); general procedure
General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product. |
- 55
-
[ 932-88-7 ]
-
[ 17873-01-7 ]
-
[ 886-66-8 ]
-
[ 3287-02-3 ]
Yield | Reaction Conditions | Operation in experiment |
1: 40%
2: 33 %Chromat. |
With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; |
Synthesis of internal alkynes (3-12); general procedure
General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product. |
- 56
-
[ 19821-84-2 ]
-
[ 17873-01-7 ]
-
[ 121866-33-9 ]
Yield | Reaction Conditions | Operation in experiment |
44% |
With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; |
Synthesis of internal alkynes (3-12); general procedure
General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product. |
- 57
-
[ 17873-01-7 ]
-
[ 932-87-6 ]
-
[ 3287-02-3 ]
Yield | Reaction Conditions | Operation in experiment |
83% |
With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; |
Synthesis of internal alkynes (3-12); general procedure
General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product. |
- 58
-
[ 17873-01-7 ]
-
[ 98-09-9 ]
-
[ 644-08-6 ]
Yield | Reaction Conditions | Operation in experiment |
87% |
With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl ammonium fluoride In N,N-dimethyl-formamide; acetonitrile at 100℃; for 3h; Inert atmosphere; Green chemistry; |
|
- 59
-
[ 570-02-5 ]
-
[ 17873-01-7 ]
-
[ 1040196-63-1 ]
Yield | Reaction Conditions | Operation in experiment |
57% |
With palladium(II) trifluoroacetate; C30H30N4; silver fluoride; In N,N-dimethyl acetamide; at 100℃; for 2h; |
General procedure: To a mixture of aryl(trialkoxy)silane(0.20 mmol), AgF (76.6 mg, 0.60 mmol), Pd(TFA)2 (5.0 mg, 0.015 mmol,7.5 mol %), and ligand 1g (6.7 mg, 0.015 mmol, 7.5 mol %) in DMAc (1.0 mL)was added arylcarboxylic acid (0.40 mmol) at room temperature under an atmosphere of air. After the mixture was stirred at 100?or 110?C for 2-8 h, the mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/EtOAc = 20:1). |
- 60
-
[ 106-37-6 ]
-
[ 17873-01-7 ]
-
[ 97295-31-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
With 2% active carbon-supported palladium; sodium hydroxide In water at 100℃; |
|
- 61
-
[ 626-39-1 ]
-
[ 17873-01-7 ]
-
[ 50446-43-0 ]
- 62
-
S-methyl-S-(p-tolyl)sulfoximine
[ No CAS ]
-
[ 17873-01-7 ]
-
N-(4-methylphenyl)-S,S-(4-methylphenyl)(methyl)sulfoximine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
79% |
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry; |
|
- 63
-
[ 17873-01-7 ]
-
[ 77970-95-7 ]
-
(4-methoxyphenyl)(methyl)(p-tolylimino)-λ6-sulfanone
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
76% |
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry; |
|
- 64
-
[ 22133-00-2 ]
-
[ 17873-01-7 ]
-
N-(4-methyl)phenyl-S-(3-chloro)phenyl-S-methylsulfoximine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
72% |
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry; |
|
- 65
-
[ 17873-01-7 ]
-
[ 4381-25-3 ]
-
rac-N-[(4-methyl)-phenyl]-S-phenyl-S-methylsulfoximine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry; |
|
- 66
-
C11H16FO4P
[ No CAS ]
-
[ 17873-01-7 ]
-
[ 1352918-73-0 ]
Yield | Reaction Conditions | Operation in experiment |
94% |
With 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; |
Hiyama Cross-Coupling; General Procedure:
General procedure: An oven dried Schlenk tube with Pd(OAc)2 (5 mol%) and dppp (10 mol%) was evacuated and purged with argon three times. A mixture of TBAF (1 M in THF, 0.36 mL), 2a (0.45 mmol), and benzylic phosphate (1a; 0.30 mmol) was dissolved in freshly distilled 1,4-dioxane (1.0 mL), and added at r.t. The reaction mixture was heated with stirring at 100 °C for 24 h, then cooled to ambient temperature and transferred to around-bottom flask. Silica gel (2.0 g) was added and the solvent was removed under reduced pressure to afford a free flowing powder. The powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum as the eluent to give the desired product 3aa. |
Reference:
[1]Zhang, Pengbo; Xu, Jian; Gao, Yuzhen; Li, Xueqin; Tang, Guo; Zhao, Yufen
[Synlett, 2014, vol. 25, # 20, p. 2928 - 2932]
- 67
-
[ 17873-01-7 ]
-
[ 128732-38-7 ]
-
1-(4-methylbenzyl)-3-(trifluoromethyl)benzene
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
86% |
With 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; |
Hiyama Cross-Coupling; General Procedure:
General procedure: An oven dried Schlenk tube with Pd(OAc)2 (5 mol%) and dppp (10 mol%) was evacuated and purged with argon three times. A mixture of TBAF (1 M in THF, 0.36 mL), 2a (0.45 mmol), and benzylic phosphate (1a; 0.30 mmol) was dissolved in freshly distilled 1,4-dioxane (1.0 mL), and added at r.t. The reaction mixture was heated with stirring at 100 °C for 24 h, then cooled to ambient temperature and transferred to around-bottom flask. Silica gel (2.0 g) was added and the solvent was removed under reduced pressure to afford a free flowing powder. The powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum as the eluent to give the desired product 3aa. |
Reference:
[1]Zhang, Pengbo; Xu, Jian; Gao, Yuzhen; Li, Xueqin; Tang, Guo; Zhao, Yufen
[Synlett, 2014, vol. 25, # 20, p. 2928 - 2932]
- 68
-
[ 7145-06-4 ]
-
[ 17873-01-7 ]
-
[ 21895-16-9 ]
Yield | Reaction Conditions | Operation in experiment |
95% |
With 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; |
Hiyama Cross-Coupling; General Procedure:
General procedure: An oven dried Schlenk tube with Pd(OAc)2 (5 mol%) and dppp (10 mol%) was evacuated and purged with argon three times. A mixture of TBAF (1 M in THF, 0.36 mL), 2a (0.45 mmol), and benzylic phosphate (1a; 0.30 mmol) was dissolved in freshly distilled 1,4-dioxane (1.0 mL), and added at r.t. The reaction mixture was heated with stirring at 100 °C for 24 h, then cooled to ambient temperature and transferred to around-bottom flask. Silica gel (2.0 g) was added and the solvent was removed under reduced pressure to afford a free flowing powder. The powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum as the eluent to give the desired product 3aa. |
Reference:
[1]Zhang, Pengbo; Xu, Jian; Gao, Yuzhen; Li, Xueqin; Tang, Guo; Zhao, Yufen
[Synlett, 2014, vol. 25, # 20, p. 2928 - 2932]
- 69
-
[ 1428524-92-8 ]
-
[ 17873-01-7 ]
-
ethyl 2-(pyridin-3-yl)-2-(p-tolyl)acetate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
61% |
With [Rh(OH)(cod)]2; tetrabutyl ammonium fluoride; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 5h; Inert atmosphere; |
|
Reference:
[1]Xia, Ying; Liu, Zhen; Feng, Sheng; Ye, Fei; Zhang, Yan; Wang, Jianbo
[Organic Letters, 2015, vol. 17, # 4, p. 956 - 959]
- 70
-
[ 17873-01-7 ]
-
[ 72410-67-4 ]
-
tert-butyl 2-phenyl-2-(p-tolyl)acetate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
72% |
With [Rh(OH)(cod)]2; tetrabutyl ammonium fluoride; tricyclohexylphosphine tetrafluoroborate In tetrahydrofuran; water at 80℃; for 5h; Inert atmosphere; |
|
Reference:
[1]Xia, Ying; Liu, Zhen; Feng, Sheng; Ye, Fei; Zhang, Yan; Wang, Jianbo
[Organic Letters, 2015, vol. 17, # 4, p. 956 - 959]
- 71
-
[ 170891-76-6 ]
-
[ 17873-01-7 ]
-
2,2-dimethyl-N-(quinolin-8-yl)-3-(p-tolyloxy)propanamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
79% |
With di-<i>tert</i>-butyl dicarbonate; copper diacetate; sodium pivalate; cesium fluoride; silver(l) oxide In N,N-dimethyl-formamide at 150℃; for 0.5h; Sealed tube; Inert atmosphere; regioselective reaction; |
|
- 72
-
[ 17873-01-7 ]
-
[ 15163-59-4 ]
-
[ 70680-21-6 ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With copper (II)-fluoride; [Pd(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(naphthoquinone)]2; silver carbonate In N,N-dimethyl acetamide at 130℃; for 19h; Inert atmosphere; Sealed tube; Glovebox; |
|
- 73
-
[ 591-50-4 ]
-
[ 17873-01-7 ]
-
[ 644-08-6 ]
Yield | Reaction Conditions | Operation in experiment |
83% |
With potassium fluoride; tetra-(n-butyl)ammonium iodide In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; |
General Procedure for Hiyama Cross-Coupling Reactions.
General procedure: A typical procedure for the cross-coupling reaction using the nanocrystals is as follows: degassed N,N'-dimethylacetamide (DMA) (1.0 mL), aryl halide (0.5 mmol), trimethoxyphenylsilane (1.5 mmol), KF (1.5 mmol), tetrabutylammonium iodide (TBAI) (0.1 mmol), and Pd-Fe3O4 catalyst (1 mol%) were added to a vial, which was equipped with a magnetic bar and purged with argon gas. The vial was sealed and the reaction mixture was heated to 150 °C for 16 h with vigorous stirring. After the reaction, the mixture was cooled to room temperature and the catalyst was collected using an external magnet. The solution containing products was diluted and extracted between dichloromethane (10 mL) and H2O(10 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography using a 1:6 mixture of ethyl acetate and n-hexane as an eluent to furnish the desired products. |
- 74
-
[ 3389-54-6 ]
-
[ 17873-01-7 ]
-
(4'-methyl-[1,1'-biphenyl]-2-yl)(pyrrolidin-1-yl)methanone
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
89% |
With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In tetrahydrofuran at 140℃; for 20h; |
|
- 75
-
[ 221044-05-9 ]
-
[ 17873-01-7 ]
-
[ 1608124-60-2 ]
Yield | Reaction Conditions | Operation in experiment |
87% |
With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water at 140℃; for 20h; Inert atmosphere; Green chemistry; |
|
71% |
With copper (II)-fluoride; oxygen; cobalt(III) acetylacetonate In toluene at 160℃; for 24h; Sealed tube; |
|
Reference:
[1]Nareddy, Pradeep; Jordan, Frank; Szostak, Michal
[Organic Letters, 2018, vol. 20, # 2, p. 341 - 344]
[2]Lu, Ming-Zhu; Ding, Xin; Shao, Changdong; Hu, Zhengsong; Luo, Haiqing; Zhi, Sanjun; Hu, Huayou; Kan, Yuhe; Loh, Teck-Peng
[Organic Letters, 2020, vol. 22, # 7, p. 2663 - 2668]
- 76
-
[ 17873-01-7 ]
-
diethyl 2,2′-disulfanediylbis(6-methyl-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate)
[ No CAS ]
-
[ 1048007-29-9 ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With copper(I) thiophene-2-carboxylate; tetrabutyl ammonium fluoride; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 60℃; for 24h; Sealed tube; Schlenk technique; Inert atmosphere; |
2.2 General Procedure for synthesis 3a-6c.
General procedure: Disulfide 1a (0.2 mmol, 0.1094 g), Pd(OAc)2 (3 mol %), CuTC (3.0 equiv), PCy3 (6 mol %), was added respectively to the sealed Schlenktube, Then phenyltrimethoxysilane 2a (3.0 equiv, 0.6 mmol, 0.1188 g), TBAF (3.0 equiv, 0.6 mmol) and solvent THF (2 mL) was injectedinto the sealed tube by syringe in the presence of nitrogen. The mixture was stirred at 60 °C for 24 h. And the progress of the reaction wasmonitored by thin-layer chromatography (silica gel). After completion of the reaction, mixture was cooled to ambient temperature,quenched by addition of saturated NH4Cl (2 mL), and extracted with ethyl acetate (3×10 mL). The organic layers were combined and driedwith anhydrous MgSO4 and concentrated in vacuo, the resulting residue was purified by silica gel column chromatography using ethylacetate/petroleum ether (1:50) as eluent to afford the products (3a-6c). |
- 77
-
[ 67-56-1 ]
-
[ 931-70-4 ]
-
[ 17873-01-7 ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With graphene immobilized iridium complex containing N-heterocyclic carbene ligand functionalized with pyrene at 30℃; for 0.333333h; |
|
- 78
-
[ 7188-38-7 ]
-
[ 17873-01-7 ]
-
[ 62-53-3 ]
-
N-(tert-butyl)-4-methyl-N'-phenylbenzimidamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
67% |
With potassium fluoride; copper diacetate; palladium dichloride In N,N-dimethyl-formamide at 120℃; for 24h; |
|
- 79
-
[ 201230-82-2 ]
-
[ 17873-01-7 ]
-
[ 62-53-3 ]
-
[ 6833-18-7 ]
Yield | Reaction Conditions | Operation in experiment |
88% |
With copper (II)-fluoride; bis(triphenylphosphine)palladium(II) dichloride In acetonitrile at 80℃; for 24h; Schlenk technique; |
|
88% |
With copper (II)-fluoride; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 80℃; for 24h; Sealed tube; |
10 Preparation of 4-methyl-N-phenylbenzamide
0.75 mmol of p-methyl(trimethoxy)phenylsilane 10 mol% Pd(PPh3)Cl2 and 2equiv.CuF2 were dissolved in 3 mL CH3CN Shrek tube (with magnetic stirrer), and the reaction tube was closed from the reaction tube. The branch pipe is filled with carbon monoxide, filled with balloons and then emptied, three times, until the air is completely emptied, then the balloon is filled, then 0.5 mmol of aniline was added to the reaction tube, and the mixture was stirred under heating at 80 ° C for 24 hours. The reaction was monitored by TLC. After the reaction was completed, the mixture was extracted three times with 10 mL of ethyl acetate. 92.8 mg of a white solid compound was obtained in a yield of 88%. |
Reference:
[1]Zhang, Jin; Hou, Yanyan; Ma, Yangmin; Szostak, Michal
[Journal of Organic Chemistry, 2019, vol. 84, # 1, p. 338 - 345]
[2]Current Patent Assignee: SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN109180518, 2019, A
Location in patent: Paragraph 0121; 0122; 0123; 0124
- 80
-
[ 1182669-71-1 ]
-
[ 17873-01-7 ]
-
4′-methyl-3-methyl-N-(quinolin-8-yl)-[1,1′-biphenyl]-2-carboxamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
66% |
With copper (II)-fluoride; cobalt(II) acetate; cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 20h; Schlenk technique; Inert atmosphere; |
|
- 81
-
[ 33757-48-1 ]
-
[ 17873-01-7 ]
-
4'-methyl-N-(quinolin-8-yl)-[1,1'-biphenyl]-2-carboxamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
63% |
With copper (II)-fluoride; cobalt(II) acetate; cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 20h; Schlenk technique; Inert atmosphere; |
|
- 82
-
[ 17873-01-7 ]
-
(1-fluoro-2,2-diiodovinyl)benzene
[ No CAS ]
-
(Z)-1-(2-fluoro-2-phenylethenyl)-4-methylbenzene
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 80℃; for 20h; regioselective reaction; |
|
- 83
-
[ 2441-97-6 ]
-
[ 17873-01-7 ]
-
(–)-(S)-3-(4-methylphenyl)cyclohexene
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
53% |
With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In tetrahydrofuran for 3h; Reflux; enantioselective reaction; |
|
- 84
-
[ 17873-01-7 ]
-
N-tert-butoxycarbonyl-5-chloro-3-piperidene
[ No CAS ]
-
(–)-tert-butyl (S)-3-(p-tolyl)-3,6-dihydropyridine-1(2H)-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
40% |
With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In tetrahydrofuran for 3h; Reflux; enantioselective reaction; |
|
- 85
-
[ 1506-76-9 ]
-
[ 17873-01-7 ]
-
[ 121-44-8 ]
-
C126H90O24Si6(6-)*6C6H15N*6H(1+)
[ No CAS ]
- 86
-
[ 17873-01-7 ]
-
N,N,N-trimethyl-1-(4-cyanophenyl)methanaminium trifluoromethanesulfonate
[ No CAS ]
-
[ 71947-05-2 ]
Yield | Reaction Conditions | Operation in experiment |
97% |
With dichloro bis(acetonitrile) palladium(II); tetrabutyl ammonium fluoride; cyclohexyldiphenylphosphine In ethanol at 120℃; for 24h; Inert atmosphere; Schlenk technique; |
|
Reference:
[1]Han, Chunyu; Zhang, Zhenming; Xu, Silin; Wang, Kai; Chen, Kaiting; Zhao, Junfeng
[Journal of Organic Chemistry, 2019, vol. 84, # 24, p. 16308 - 16313]
- 87
-
[ 573-57-9 ]
-
[ 17873-01-7 ]
-
[ 1505513-83-6 ]
-
(1R,2S)-2-(4-methylphenyl)-1,2-dihydronaphthalen-1-ol
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
83 % ee |
With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); tris-(dibenzylideneacetone)dipalladium(0); CuF2*H2O In water; 1,2-dichloro-ethane at 20℃; Overall yield = 89 percent; Overall yield = 42.1 mg; enantioselective reaction; |
|
Reference:
[1]Tan, Yun; Yao, Yongqi; Yang, Wen; Lin, Qifu; Huang, Guobao; Tan, Minxiong; Chen, Shuqi; Chen, Donghan; Yang, Dingqiao
[Advanced Synthesis and Catalysis, 2020, vol. 362, # 1, p. 139 - 145]