Name: 16356-02-8|1,4-Dimethoxy-2-butyne|98%
Brand: Ambeed
SKU: A788848
Price: 6.0 USD
Availability: InStock
Rating: 92 (29 reviews)

1
[ 16356-02-8 ]
[ 13179-96-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; nickel at 170℃;
	With hydrogen; platinum

Reference： [1]Gauthier,D. [Annales de Chimie (Cachan, France), 1909, vol. <8> 16, p. 332]
[2]Dupont; Rouviere [Annales de Chimie (Cachan, France), 1913, vol. <8>30, p. 525]

2
[ 16356-02-8 ]
[ 40206-02-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dicobalt octacarbonyl In toluene at 230℃; for 0.0833333h; Flow reactor;
50%	In tetrahydrofuran at 30℃; Heating;
	With sodium tetrahydroborate In hexane at 82.5℃; for 66h; effect of use of var. catalysts, and var. times, and var. temp.;

	With sodium tetrahydroborate In hexane at 82.5℃; for 66h; Yield given;
	at 60℃; for 6h; Yield given;
40.5 g	With sodium tetrahydroborate; tricyclohexylphosphine In hexane at 82.5℃; for 120h;

Reference： [1]García-Lacuna, Jorge; Domínguez, Gema; Blanco-Urgoiti, Jaime; Pérez-Castells, Javier [Organic Letters, 2018, vol. 20, # 17, p. 5219 - 5223]
[2]Alphonse, P.; Moyen, F.; Mazerolles, P. [Journal of Organometallic Chemistry, 1988, vol. 345, p. 209 - 216]
[3]Schulz, Wolfgang; Rosenthal, Uwe [Zeitschrift fur Chemie, 1986, vol. 26, # 5, p. 176 - 177]
[4]Schulz, Wolfgang; Rosenthal, Uwe [Zeitschrift fur Chemie, 1986, vol. 26, # 5, p. 176 - 177]
[5]Rosenthal, Uwe; Schulz, Wolfgang [Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 3, p. 335 - 341]
[6]Rosenthal, U.; Schulz, W. [Journal of Organometallic Chemistry, 1987, vol. 321, p. 103 - 118]

3
[ 998-30-1 ]
[ 16356-02-8 ]
(E)-1,4-dimethoxy-1-triethoxysilyl-2-buten [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In tetrahydrofuran for 2h; Ambient temperature;
	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 100℃; for 2h; Green chemistry;	(a) Procedure for hydrosilylation of alkynes performed in toluene or THF General procedure: A silane and an appropriate alkyne were placed in a 25cm3 round bottom flask equipped with a stirrer and a glass stopper. The reagents were dissolved in toluene or THF and Karstedt’s catalyst was added. Subsequently, the reaction mixture was heated to 60°C or 100°C, depending on the reaction. Samples of the reaction mixture were collected in intervals, and the conversion of SiH was determined by 1H NMR and GC-MS. Then the reactions were repeated in determined reaction time, and the resulting mixtures were isolated by the evaporation of the solvent under vacuum. Products were characterized by 1H, 13C, 29Si NMR, GC-MS analysis. The platinum residue was removed by filtration of petroleum ether solution through silica gel. After evaporation of solvents, the products were dried for 6h under vacuum. Isolated products were characterized by 1H, 13C, 29Si NMR, GC-MS. For new compounds, elemental analysis was performed as well.

Reference： [1]Brockmann, Monika; Dieck, Heindirk tom; Klaus, Juergen [Journal of Organometallic Chemistry, 1986, vol. 301, p. 209 - 226]
[2]Stefanowska, Kinga; Franczyk, Adrian; Szyling, Jakub; Salamon, Katarzyna; Marciniec, Bogdan; Walkowiak, Jedrzej [Journal of Catalysis, 2017, vol. 356, p. 206 - 213]

4
[ 16356-02-8 ]
[ 789-25-3 ]
(E)-1,4-dimethoxy-1-triphenylsilyl-2-buten [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In tetrahydrofuran for 24h; Ambient temperature;
	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 100℃; for 6h; Green chemistry;	(a) Procedure for hydrosilylation of alkynes performed in toluene or THF General procedure: A silane and an appropriate alkyne were placed in a 25cm3 round bottom flask equipped with a stirrer and a glass stopper. The reagents were dissolved in toluene or THF and Karstedt’s catalyst was added. Subsequently, the reaction mixture was heated to 60°C or 100°C, depending on the reaction. Samples of the reaction mixture were collected in intervals, and the conversion of SiH was determined by 1H NMR and GC-MS. Then the reactions were repeated in determined reaction time, and the resulting mixtures were isolated by the evaporation of the solvent under vacuum. Products were characterized by 1H, 13C, 29Si NMR, GC-MS analysis. The platinum residue was removed by filtration of petroleum ether solution through silica gel. After evaporation of solvents, the products were dried for 6h under vacuum. Isolated products were characterized by 1H, 13C, 29Si NMR, GC-MS. For new compounds, elemental analysis was performed as well.

Reference： [1]Brockmann, Monika; Dieck, Heindirk tom; Klaus, Juergen [Journal of Organometallic Chemistry, 1986, vol. 301, p. 209 - 226]
[2]Stefanowska, Kinga; Franczyk, Adrian; Szyling, Jakub; Salamon, Katarzyna; Marciniec, Bogdan; Walkowiak, Jedrzej [Journal of Catalysis, 2017, vol. 356, p. 206 - 213]

5
[ 16356-02-8 ]
[ 3685-20-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With ammonia; sodium amide; ferric nitrate for 1h;
88%	With sodium In ammonia
	With Iron(III) nitrate nonahydrate; ammonia; sodium at -78 - 20℃; for 3h; Inert atmosphere;

With Iron(III) nitrate nonahydrate; ammonia; sodium In hexane; cyclohexane at -78 - 23℃; for 1h; Inert atmosphere; Schlenk technique;

Reference： [1]Adams, Harry; Anderson, James C.; Bell, Richard; Jones, D. Neville; Peel, Michael R.; Tomkinson, Nicholas C. O. [Journal of the Chemical Society. Perkin transactions I, 1998, # 23, p. 3967 - 3973]
[2]Gao, Xuri; Hall, Dennis G. [Tetrahedron Letters, 2003, vol. 44, # 10, p. 2231 - 2235]
[3]Kou, Kevin G. M.; Li, Beryl X.; Lee, Jack C.; Gallego, Gary M.; Lebold, Terry P.; Dipasquale, Antonio G.; Sarpong, Richmond [Journal of the American Chemical Society, 2016, vol. 138, # 34, p. 10830 - 10833]
[4]Kou, Kevin G. M.; Kulyk, Svitlana; Marth, Christopher J.; Lee, Jack C.; Doering, Nicolle A.; Li, Beryl X.; Gallego, Gary M.; Lebold, Terry P.; Sarpong, Richmond [Journal of the American Chemical Society, 2017, vol. 139, # 39, p. 13882 - 13896]

6
[ 2142-69-0 ]
[ 16356-02-8 ]
2,3-bis(methoxymethyl)-1-methyl-1H-inden-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With palladium diacetate; ethanol; potassium acetate In N,N-dimethyl-formamide at 100℃; for 20h;

Reference： [1]Quan, Long Guo; Gevorgyan, Vladimir; Yamamoto, Yoshinori [Journal of the American Chemical Society, 1999, vol. 121, # 14, p. 3545 - 3546]

7
[ 13047-06-8 ]
[ 16356-02-8 ]
2,3-bis-methoxymethyl-1-phenyl-1<i>H</i>-inden-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With palladium diacetate; ethanol; potassium acetate In N,N-dimethyl-formamide at 100℃; for 28h;

Reference： [1]Quan, Long Guo; Gevorgyan, Vladimir; Yamamoto, Yoshinori [Journal of the American Chemical Society, 1999, vol. 121, # 14, p. 3545 - 3546]

8
[ 88284-48-4 ]
[ 16356-02-8 ]
[ 101789-64-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With cesium fluoride; tris-(o-tolyl)phosphine In acetonitrile at 60℃; for 4h;
59%	With palladium diacetate; cesium fluoride; tris-(o-tolyl)phosphine In acetonitrile at 60℃; for 4h;

Reference： [1]Radhakrishnan; Yoshikawa, Eiji; Yamamoto, Yoshinori [Tetrahedron Letters, 1999, vol. 40, # 42, p. 7533 - 7535]
[2]Yoshikawa, Eiji; Radhakrishnan; Yamamoto, Yoshinori [Journal of the American Chemical Society, 2000, vol. 122, # 30, p. 7280 - 7286]

9
[ 16356-02-8 ]
[ 13179-96-9 ]

Yield	Reaction Conditions	Operation in experiment
	at 170℃;

Reference： [1]Gauthier,D. [Annales de Chimie (Cachan, France), 1909, vol. <8> 16, p. 332]

10
[ 16356-02-8 ]
[ 67-56-1 ]
[ 628-28-4 ]
[ 13179-96-9 ]

Yield	Reaction Conditions	Operation in experiment
	Hydrogenation;

Reference： [1]Rouviere bei Dupont [Annales de Chimie (Cachan, France), 1913, vol. <8>30, p. 525]

11
[ 75-15-0 ]
[ 89424-83-9 ]
[ 16356-02-8 ]
5-(4,5-bis-methoxymethyl-[1,3]dithiol-2-ylidenemethyl)-1,3-dihydro-isobenzofuran [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 152,p. 185 - 190

12
[ 4873-09-0 ]
[ 16356-02-8 ]
1,2,3,4-tetrakis(methoxymethyl)-5-methylbenzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5961 - 5966
[2]Organic Letters,2000,vol. 2,p. 655 - 657

13
[ 88284-48-4 ]
[ 107-05-1 ]
[ 16356-02-8 ]
[ 883-20-5 ]
1,2-bis-methoxymethyl-3-methyl-naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 50% 2: 4%	Stage #1: 3-chloroprop-1-ene; 1,4-dimethoxy-2-butyne With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; cesium fluoride In tetrahydrofuran; acetonitrile at 20℃; for 0.0833333h; Stage #2: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With cesium fluoride In tetrahydrofuran; acetonitrile at 60℃; for 24h;

Reference： [1]Yoshikawa, Eiji; Radhakrishnan; Yamamoto, Yoshinori [Journal of the American Chemical Society, 2000, vol. 122, # 30, p. 7280 - 7286]

14
[ 107428-05-7 ]
[ 16356-02-8 ]
5,6-bis-methoxymethyl-4,7-dimethyl-indan-2,2-dicarboxylic acid dimethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With 1,2-bis-(diphenylphosphino)ethane In benzene at 20℃; for 0.5h;
94%	With 1,2-bis-(diphenylphosphino)ethane In benzene at 20℃; for 0.5h;

Reference： [1]Takeuchi, Ryo; Tanaka, Shigeru; Nakaya, Yoshihiko [Tetrahedron Letters, 2001, vol. 42, # 16, p. 2991 - 2994]
[2]Kezuka, Satoko; Tanaka, Shigeru; Ohe, Toshihito; Nakaya, Yoshihiko; Takeuchi, Ryo [Journal of Organic Chemistry, 2006, vol. 71, # 2, p. 543 - 552]

15
[ 75999-66-5 ]
[ 16356-02-8 ]
3,4-dimethoxymethyl-6-methoxy-2-trifluoromethylquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine; 1,2-bis-(diphenylphosphino)ethane In toluene at 110℃;

Reference： [1]Amii; Kishikawa; Uneyama [Organic letters, 2001, vol. 3, # 8, p. 1109 - 1112]

16
[ 38053-91-7 ]
[ 16356-02-8 ]
[(4,5-bis(methoxymethyl)-1,4-cyclohexadien-1-yl)oxy]trimethylsilane [ No CAS ]

Reference： [1]Synthesis,2004,p. 634 - 638
[2]Synlett,2002,p. 1081 - 1084
[3]Synthesis,2012,vol. 44,p. 1293 - 1303

17
[ 110-67-8 ]
[ 16356-02-8 ]
2-(2-methoxyethyl)-3,4,5,6-tetra(methoxymethyl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 4414 - 4422

18
[ 762-42-5 ]
[ 16356-02-8 ]
[ 109552-63-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 50℃; for 2h;

Reference： [1]Takeuchi, Ryo; Nakaya, Yoshihiko [Organic Letters, 2003, vol. 5, # 20, p. 3659 - 3662]

19
[ 762-42-5 ]
[ 16356-02-8 ]
[ 109552-63-8 ]
dimethyl 3,4,5,6-tetrakis(methoxymethyl)-1,2-benzenedicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 96% 2: 1%	With 1,2-bis(di(pentafluorophenyl)phosphino)ethane In tetrahydrofuran at 50℃; for 1h;

Reference： [1]Takeuchi, Ryo; Nakaya, Yoshihiko [Organic Letters, 2003, vol. 5, # 20, p. 3659 - 3662]

20
[ 16356-02-8 ]
bis[3-(2-methylphenyl)prop-2-yl] ether [ No CAS ]
1,3-dihydro-5,6-bis(methoxymethyl)-4,7-bis(2-methylphenyl)isobenzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S)-1,2-bis(2,5-dimethylphospholano)benzene In xylene at 100℃; for 1h;

Reference： [1]Shibata, Takanori; Fujimoto, Takayoshi; Yokota, Kazuhisa; Takagi, Kentaro [Journal of the American Chemical Society, 2004, vol. 126, # 27, p. 8382 - 8383]

21
[ 16356-02-8 ]
bis[3-(2-chlorophenyl)prop-2-yl] ether [ No CAS ]
1,3-dihydro-5,6-bis(methoxymethyl)-4,7-bis(2-chlorophenyl)isobenzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S)-1,2-bis(2,5-dimethylphospholano)benzene In xylene at 100℃; for 1h;

Reference： [1]Shibata, Takanori; Fujimoto, Takayoshi; Yokota, Kazuhisa; Takagi, Kentaro [Journal of the American Chemical Society, 2004, vol. 126, # 27, p. 8382 - 8383]

22
[ 16356-02-8 ]
(Z)-1,8-di(naphthalen-1-yl)oct-4-en-1,7-diyne [ No CAS ]
2',3'-dimethoxymethyl-1,1':4',1''-ter-5',8'-dihydronaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S)-1,2-bis(2,5-dimethylphospholano)benzene In xylene at 100℃; for 1h;

Reference： [1]Shibata, Takanori; Fujimoto, Takayoshi; Yokota, Kazuhisa; Takagi, Kentaro [Journal of the American Chemical Society, 2004, vol. 126, # 27, p. 8382 - 8383]

23
[ 16356-02-8 ]
1,7-di(naphthalen-1-yl)hepta-1,6-diyne [ No CAS ]
2,3-dihydro-4,7-di(naphthalen-1-yl)-5,6-bis(methoxymethyl)-1H-indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S)-1,2-bis(2,5-dimethylphospholano)benzene In xylene at 100℃; for 1h;

Reference： [1]Shibata, Takanori; Fujimoto, Takayoshi; Yokota, Kazuhisa; Takagi, Kentaro [Journal of the American Chemical Society, 2004, vol. 126, # 27, p. 8382 - 8383]

24
[ 16356-02-8 ]
bis[3-(4-methoxynaphthalen-1-yl)prop-2-yl] ether [ No CAS ]
1,3-dihydro-5,6-bis(methoxymethyl)-4,7-bis(4-methoxynaphthalen-1-yl)isobenzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S)-1,2-bis(2,5-dimethylphospholano)benzene In xylene at 100℃; for 1h;

Reference： [1]Shibata, Takanori; Fujimoto, Takayoshi; Yokota, Kazuhisa; Takagi, Kentaro [Journal of the American Chemical Society, 2004, vol. 126, # 27, p. 8382 - 8383]

25
[ 16356-02-8 ]
4-methyl-N,N-bis(3-(naphthalen-1-yl)prop-2-yn-1-yl)benzenesulfonamide [ No CAS ]
1,3-dihydro-4,7-di(naphthalen-1-yl)-5,6-bis(methoxymethyl)-2-tosylisoindoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S)-1,2-bis(2,5-dimethylphospholano)benzene In xylene at 100℃; for 1h;

Reference： [1]Shibata, Takanori; Fujimoto, Takayoshi; Yokota, Kazuhisa; Takagi, Kentaro [Journal of the American Chemical Society, 2004, vol. 126, # 27, p. 8382 - 8383]

26
[ 16356-02-8 ]
1,7-di(naphthalen-1-yl)-4,4-bis(ethoxycarbonyl)hepta-1,6-diyne [ No CAS ]
2,3-dihydro-4,7-di(naphthalen-1-yl)-2,2-bis(ethoxycarbonyl)-5,6-bis(methoxymethyl)-1H-indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S)-1,2-bis(2,5-dimethylphospholano)benzene In xylene at 100℃; for 1h;

Reference： [1]Shibata, Takanori; Fujimoto, Takayoshi; Yokota, Kazuhisa; Takagi, Kentaro [Journal of the American Chemical Society, 2004, vol. 126, # 27, p. 8382 - 8383]

27
[ 2787-43-1 ]
[ 201230-82-2 ]
[ 16356-02-8 ]
2,3-Bis-methoxymethyl-5-((E)-1-methyl-propenyl)-cyclopent-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With di(rhodium)tetracarbonyl dichloride; (Z)-3-methyl-1,3-pentadiene In 1,2-dichloro-ethane at 60℃; for 22h;

Reference： [1]Wender, Paul A.; Deschamps, Nicole M.; Williams, Travis J. [Angewandte Chemie - International Edition, 2004, vol. 43, # 23, p. 3076 - 3079]

28
[ 201230-82-2 ]
[ 62640-74-8 ]
[ 16356-02-8 ]
5-benzyl-5-(1-benzyl-vinyl)-2,3-bis-methoxymethyl-cyclopent-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With di(rhodium)tetracarbonyl dichloride; (Z)-3-methyl-1,3-pentadiene In 1,2-dichloro-ethane at 60℃; for 9h;

Reference： [1]Wender, Paul A.; Deschamps, Nicole M.; Williams, Travis J. [Angewandte Chemie - International Edition, 2004, vol. 43, # 23, p. 3076 - 3079]

29
[ 762-21-0 ]
[ 16356-02-8 ]
5,6-bis(methoxymethyl)benzene-1,2,3,4-tetracarboxylic acid tetraethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With 2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In dichloromethane at 20℃; for 16h;

Reference： [1]Tanaka, Ken; Nishida, Goushi; Ogino, Masakazu; Hirano, Masao; Noguchi, Keiichi [Organic Letters, 2005, vol. 7, # 14, p. 3119 - 3121]

30
[ 132330-45-1 ]
[ 16356-02-8 ]
3,4-bis(methoxymethyl)-6-methyl-8-tosyl-8-azabicyclo[4.3.0]nona-1,3-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With [2'-(diphenylphosphanyl)-[1,1'-binaphthalen]-2-yl]diphenylphosphane In 1,2-dichloro-ethane at 40℃; for 15h;

Reference： [1]Shibata, Takanori; Arai, Yoshikazu; Tahara, Yu-Ki [Organic Letters, 2005, vol. 7, # 22, p. 4955 - 4957]

31
[ 109930-20-3 ]
[ 16356-02-8 ]
3,4-bis(methoxymethyl)-6-methyl-8-oxabicyclo[4.3.0]nona-1,3-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With [2'-(diphenylphosphanyl)-[1,1'-binaphthalen]-2-yl]diphenylphosphane In 1,2-dichloro-ethane at 80℃; for 1h;

Reference： [1]Shibata, Takanori; Arai, Yoshikazu; Tahara, Yu-Ki [Organic Letters, 2005, vol. 7, # 22, p. 4955 - 4957]

32
[ 292607-11-5 ]
[ 16356-02-8 ]
3,4-bis(methoxymethyl)-2,6-dimethyl-8-tosyl-8-azabicyclo[4.3.0]nona-1,3-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine] In 1,2-dichloro-ethane at 60℃; for 12h;

Reference： [1]Shibata, Takanori; Arai, Yoshikazu; Tahara, Yu-Ki [Organic Letters, 2005, vol. 7, # 22, p. 4955 - 4957]

33
[ 617-86-7 ]
[ 16356-02-8 ]
(E)-(1,4-dimethoxybut-2-en-2-yl)triethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With rhodium nanaoparticle stablized by polyethylene glycol at 60℃; for 20h; Sealed tube; stereoselective reaction;
95%	With bis(1,3-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene)diiodonickel(II); diethylzinc In tetrahydrofuran; hexane at 50℃; for 2h; diastereoselective reaction;
58%	In tetrahydrofuran at 40℃; for 10h;

With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 100℃; for 2h; Green chemistry;

(a) Procedure for hydrosilylation of alkynes performed in toluene or THF General procedure: A silane and an appropriate alkyne were placed in a 25cm3 round bottom flask equipped with a stirrer and a glass stopper. The reagents were dissolved in toluene or THF and Karstedt’s catalyst was added. Subsequently, the reaction mixture was heated to 60°C or 100°C, depending on the reaction. Samples of the reaction mixture were collected in intervals, and the conversion of SiH was determined by 1H NMR and GC-MS. Then the reactions were repeated in determined reaction time, and the resulting mixtures were isolated by the evaporation of the solvent under vacuum. Products were characterized by 1H, 13C, 29Si NMR, GC-MS analysis. The platinum residue was removed by filtration of petroleum ether solution through silica gel. After evaporation of solvents, the products were dried for 6h under vacuum. Isolated products were characterized by 1H, 13C, 29Si NMR, GC-MS. For new compounds, elemental analysis was performed as well.

Reference： [1]Guo, Wusheng; Pleixats, Roser; Shafir, Alexandr; Parella, Teodor [Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 89 - 99]
[2]Location in patent: experimental part Berding, Joris; Van Paridon, John A.; Van Rixel, Vincent H. S.; Bouwman, Elisabeth [European Journal of Inorganic Chemistry, 2011, # 15, p. 2450 - 2458]
[3]Yong, Li; Kirleis, Karin; Butenschoen, Holger [Advanced Synthesis and Catalysis, 2006, vol. 348, # 7-8, p. 833 - 836]
[4]Stefanowska, Kinga; Franczyk, Adrian; Szyling, Jakub; Salamon, Katarzyna; Marciniec, Bogdan; Walkowiak, Jedrzej [Journal of Catalysis, 2017, vol. 356, p. 206 - 213]

34
[ 922501-37-9 ]
[ 16356-02-8 ]
2,3-bis(methoxymethyl)-9,9-dimethyl-1,4-diphenyl-9-silafluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In dibutyl ether at 110℃; for 24h;

Reference： [1]Matsuda, Takanori; Kadowaki, Sho; Goya, Tsuyoshi; Murakami, Masahiro [Organic Letters, 2007, vol. 9, # 1, p. 133 - 136]

35
[ 922501-47-1 ]
[ 16356-02-8 ]
2,3-bis(methoxymethyl)-9,9-dimethyl-1-pentyl-4-phenyl-9-silafluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In dibutyl ether at 110℃; for 24h;

Reference： [1]Matsuda, Takanori; Kadowaki, Sho; Goya, Tsuyoshi; Murakami, Masahiro [Organic Letters, 2007, vol. 9, # 1, p. 133 - 136]

36
[ 922501-45-9 ]
[ 16356-02-8 ]
2,3-bis(methoxymethyl)-9,9-dimethyl-1-phenyl-4-(4-vinylphenyl)-9-silafluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In dibutyl ether at 110℃; for 24h;

Reference： [1]Matsuda, Takanori; Kadowaki, Sho; Goya, Tsuyoshi; Murakami, Masahiro [Organic Letters, 2007, vol. 9, # 1, p. 133 - 136]

37
[ 922501-48-2 ]
[ 16356-02-8 ]
2,3-bis(methoxymethyl)-9,9-dimethyl-1,4-dipentyl-9-silafluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In dibutyl ether at 145℃; for 24h;

Reference： [1]Matsuda, Takanori; Kadowaki, Sho; Goya, Tsuyoshi; Murakami, Masahiro [Organic Letters, 2007, vol. 9, # 1, p. 133 - 136]

38
[ 922501-46-0 ]
[ 16356-02-8 ]
2,3-bis(methoxymethyl)-1,4-bis(4-methoxyphenyl)-9,9-dimethyl-9-silafluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In dibutyl ether at 110℃; for 24h;

Reference： [1]Matsuda, Takanori; Kadowaki, Sho; Goya, Tsuyoshi; Murakami, Masahiro [Organic Letters, 2007, vol. 9, # 1, p. 133 - 136]

39
[ 922501-61-9 ]
[ 16356-02-8 ]
6,7-dimethoxy-2,3-bis(methoxymethyl)-9,9-dimethyl-1,4-diphenyl-9-silafluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In dibutyl ether at 110℃; for 24h;

Reference： [1]Matsuda, Takanori; Kadowaki, Sho; Goya, Tsuyoshi; Murakami, Masahiro [Organic Letters, 2007, vol. 9, # 1, p. 133 - 136]

40
bis(phenylethynyl)bis[2-(phenylethynyl)phenyl]silane [ No CAS ]
[ 16356-02-8 ]
1,1',4,4'-tetraphenyl-2,2',3,3'-tetrakis(methoxymethyl)-9,9'-spirobi(9-silafluorene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In dibutyl ether at 145℃; for 24h;

Reference： [1]Matsuda, Takanori; Kadowaki, Sho; Goya, Tsuyoshi; Murakami, Masahiro [Organic Letters, 2007, vol. 9, # 1, p. 133 - 136]

41
[ 27258-80-6 ]
[ 16356-02-8 ]
2,3-dimethoxymethyl-1,4-diphenylanthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole In dichloromethane at 20℃; for 16h;

Reference： [1]Tanaka, Ken; Suda, Takeshi; Noguchi, Keiichi; Hirano, Masao [Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2243 - 2246]

42
C₄₂H₂₈O₂ [ No CAS ]
[ 16356-02-8 ]
1,4-bis(1,3-dihydro-5,6-bis(methoxymethyl)-4-(naphthalen-1-yl)isobenzofuran-7-yl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene In xylene at 100℃; for 0.166667h;

Reference： [1]Shibata, Takanori; Tsuchikama, Kyoji [Chemical Communications, 2005, # 48, p. 6017 - 6019]

43
C₅₆H₄₂N₂O₄S₂ [ No CAS ]
[ 16356-02-8 ]
1,4-bis(5,6-bis(methoxymethyl)-4-(naphthalen-1-yl)-2-tosylisoindolin-7-yl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene In xylene at 100℃; for 0.166667h;

Reference： [1]Shibata, Takanori; Tsuchikama, Kyoji [Chemical Communications, 2005, # 48, p. 6017 - 6019]

44
C₄₆H₃₂ [ No CAS ]
[ 16356-02-8 ]
1,4-bis(2,3-bis(methoxymethyl)-4-(naphthalen-1-yl)naphthalen-1-yl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: C₄₆H₃₂; 1,4-dimethoxy-2-butyne With 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene In xylene at 140℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In xylene Further stages.;

Reference： [1]Shibata, Takanori; Tsuchikama, Kyoji [Chemical Communications, 2005, # 48, p. 6017 - 6019]

45
[ 6921-28-4 ]
[ 16356-02-8 ]
C₁₂H₁₇NO₂*HCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: dipropargylamine With pyridine In dichloromethane at 20℃; for 12h; Stage #2: 1,4-dimethoxy-2-butyne In ethanol; dichloromethane at 60℃; for 48h; Stage #3: With hydrogenchloride In methanol; dichloromethane at 20℃; for 1h; Further stages.;

Reference： [1]Young, Douglas D.; Senaiar, Ramesh S.; Deiters, Alexander [Chemistry - A European Journal, 2006, vol. 12, # 21, p. 5563 - 5568]

46
[ 5176-28-3 ]
[ 16356-02-8 ]
(3aRS,9bSR)-tert-butyl 2,3-bis(methoxymethyl)-3a,9b-dihydro-1H-benzo[g]indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With methyl iodide In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Tenaglia, Alphonse; Marc, Sylvain [Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1397 - 1402]

47
1,4-dihydro-1,4-epiazano-naphthalene-9-carbamic acid methyl ester [ No CAS ]
[ 16356-02-8 ]
(3aRS,9bSR)-methyl 2,3-bis(methoxymethyl)-3a,9b-dihydro-1H-benzo[g]indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With methyl iodide In 1,4-dioxane at 60℃; for 22h;

Reference： [1]Tenaglia, Alphonse; Marc, Sylvain [Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1397 - 1402]

48
[ 16356-02-8 ]
[ 312753-61-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2,2-trifluoro-N-[1-(2-propynyl)-3-butynyl]-acetamide In ethanol at 80℃; for 5h;	8 Intermediate -2-(Trifluoroacetylamino)-5,6-bis(methoxymethyl)indaneAccording to the procedure of Magnus et. al (Tetrahed. Lett., 34, 23-26 (1993)) a solution of commercially available 1,4-dimethoxy-2-butyne (1.32 g, 11.5 mmol) in nitrogen-degassed ethanol is heated to 80° C. with stirring under a nitrogen atmosphere. Tris(triphenylphosphine)rhodium chloride (64 mg, 0.07 mmol) and a solution of 2,2,2-trifluoro-N-[1-(2-propynyl)-3-butynyl]-acetamide (470 mg, 2.32 mmol; prepared from literature procedure: Romero, Arthur G.; Leiby, Jeffrey A PCT Int. Appl. WO 9623760) in nitrogen-degassed ethanol (2 ml) are added in portions over 2 hours. The mixture is stirred under nitrogen at 80° C. for a further 3 hours. The solvent is removed under vacuo and the residue is purified by flash chromatography on silica gel, eluting with hexane/ethyl acetate (2:1)1H-NMR (CDCl3) ppm: 2.9 (2H, dd), 3.35 (2H, dd), 3.45 (6H, s), 4.57 (4H, s), 4.85 (1H, m), 6.4 (1H, br s), 7.30 (2H, s).

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US6878721, 2005, B1 Location in patent: Page/Page column 14-15

49
[ 6229-00-1 ]
[ 16356-02-8 ]
[ 1076068-40-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1,6-bis(diphenylphosphino)hexane In 1,4-dioxane at 80℃; for 3h;

Reference： [1]Nishimura, Takahiro; Guo, Xun-Xiang; Ohnishi, Kohei; Hayashi, Tamio [Advanced Synthesis and Catalysis, 2007, vol. 349, # 17-18, p. 2669 - 2672]

50
[ 592-41-6 ]
[ 16356-02-8 ]
C₁₂H₂₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With zinc(II) iodide; zinc In dichloromethane at 25℃; for 16h;

Reference： [1]Hilt, Gerhard; Treutwein, Jonas [Angewandte Chemie - International Edition, 2007, vol. 46, # 44, p. 8500 - 8502]

51
[ 59208-49-0 ]
[ 16356-02-8 ]
[ 1026024-29-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trimethylphosphane In toluene at 110℃; for 7h;

Reference： [1]Kajita, Yuichi; Matsubara, Seijiro; Kurahashi, Takuya [Journal of the American Chemical Society, 2008, vol. 130, # 19, p. 6058 - 6059]

52
[ 1295-35-8 ]
[ 2622-14-2 ]
[ 16356-02-8 ]
[ 113095-46-8 ]

Reference： [1]Journal of Organometallic Chemistry,1990,vol. 390,p. 113 - 120

53
[ 498-66-8 ]
[ 16356-02-8 ]
[ 1072142-84-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With Br₂Co*C₂₇H₂₆P₂; zinc(II) iodide; zinc In dichloromethane at 25℃;

Reference： [1]Treutwein, Jonas; Hilt, Gerhard [Angewandte Chemie - International Edition, 2008, vol. 47, # 36, p. 6811 - 6813]

54
dicyclopentadiene [ No CAS ]
[ 16356-02-8 ]
9,10-bis(methoxymethyl)tetracyclo[5.4.1.0(2,6).0(8,11)]dodeca-3,9-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With Br₂Co*C₂₇H₂₆P₂; zinc(II) iodide; zinc In dichloromethane at 25℃; for 16h;

Reference： [1]Treutwein, Jonas; Hilt, Gerhard [Angewandte Chemie - International Edition, 2008, vol. 47, # 36, p. 6811 - 6813]

55
[ 615-42-9 ]
[ 16356-02-8 ]
[ 1047668-20-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II); 1,2-bis-(diphenylphosphino)ethane; zinc In acetonitrile at 100℃; for 48h; Inert atmosphere;

Reference： [1]Hsieh, Jen-Chieh; Cheng, Chien-Hong [Chemical Communications, 2008, # 26, p. 2992 - 2994]

56
[ 620-80-4 ]
[ 16356-02-8 ]
[ 1111192-23-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; trimethylphosphane In toluene at 130℃;

Reference： [1]Koyama, Ichiro; Kurahashi, Takuya; Matsubara, Seijiro [Journal of the American Chemical Society, 2009, vol. 131, # 4, p. 1350 - 1351]

57
[ 18442-29-0 ]
[ 16356-02-8 ]
[ 1085921-24-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis(triphenylphosphine)nickel⁽⁰⁾ dicarbonyl In toluene at 100℃; for 0.0666667h; Microwave irradiation;

Reference： [1]McIver, Andrew; Young, Douglas D.; Deiters, Alexander [Chemical Communications, 2008, # 39, p. 4750 - 4752]

58
[ 89343-06-6 ]
[ 16356-02-8 ]
C₂₃H₄₂O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; tris-n-propylphosphine In toluene at 80℃; for 6h; Inert atmosphere;

Reference： [1]Ogata, Kenichi; Murayama, Hiroyuki; Sugasawa, Jun; Suzuki, Noriyuki; Fukuzawa, Shin-ichi [Journal of the American Chemical Society, 2009, vol. 131, p. 3176 - 3177]

59
[ 440084-09-3 ]
[ 16356-02-8 ]
[ 1132669-80-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With [(DPPP)palladium(II)(H₂O)2] triflate In 1,4-dioxane; water at 50℃; Inert atmosphere;

Reference： [1]Zhou, Feng; Yang, Miao; Lu, Xiyan [Organic Letters, 2009, vol. 11, # 6, p. 1405 - 1408]

60
C₂₁H₂₃BO₃ [ No CAS ]
[ 16356-02-8 ]
[ 1132669-83-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With [(DPPP)palladium(II)(H₂O)2] triflate In 1,4-dioxane; water at 50℃; Inert atmosphere;

Reference： [1]Zhou, Feng; Yang, Miao; Lu, Xiyan [Organic Letters, 2009, vol. 11, # 6, p. 1405 - 1408]

61
[ 89343-06-6 ]
[ 16356-02-8 ]
C₁₇H₃₂O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With dmap; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ In toluene at 50℃; for 3h; Inert atmosphere;

Reference： [1]Location in patent: scheme or table Matsuyama, Naoto; Tsurugi, Hayato; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2274 - 2278]

62
[ 1066-54-2 ]
[ 16356-02-8 ]
C₁₁H₂₀O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ In toluene at 50℃; for 3h; Inert atmosphere;

Reference： [1]Location in patent: scheme or table Matsuyama, Naoto; Tsurugi, Hayato; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2274 - 2278]

63
[ 1160757-30-1 ]
[ 16356-02-8 ]
[ 1160757-34-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1,4-diaza-bicyclo[2.2.2]octane; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane; water at 80℃; for 15h;
76%	With 1,4-diaza-bicyclo[2.2.2]octane; chloro(1,5-cyclooctadiene)rhodium(I) dimer In water; N,N-dimethyl-formamide at 80℃; for 15h; Sealed tube; Inert atmosphere;

Reference： [1]Location in patent: scheme or table Tobisu, Mamoru; Onoe, Masahiro; Kita, Yusuke; Chatani, Naoto [Journal of the American Chemical Society, 2009, vol. 131, p. 7506 - 7507]
[2]Onoe, Masahiro; Baba, Katsuaki; Kim, Yoonjoo; Kita, Yusuke; Tobisu, Mamoru; Chatani, Naoto [Journal of the American Chemical Society, 2012, vol. 134, # 47, p. 19477 - 19488]

64
[ 16356-02-8 ]
[ 110280-53-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With ammonium metavanadate; tetrabutylammomium bromide; oxygen; aluminium bromide In acetonitrile at 80℃; for 18h;
97%	With ammonium metavanadate; aluminum tri-bromide; tetrabutylammomium bromide; oxygen In acetonitrile at 80℃; for 18h;
77%	With ammonium metavanadate; tetrabutylammomium bromide; trifluoroacetic acid In 1,4-dioxane at 80℃; for 12h;

75 %Spectr.

With tetrabutylammomium bromide; dihydrogen peroxide; trifluoroacetic acid In water at 25℃; for 24h; Inert atmosphere;

2. General procedure for oxidative bromination reaction General procedure: In a 10 mL two-necked flask equipped with a reflux condenser, substrate (0.25mmol) and tetrabutylammonium bromide (161.2 mg, 0.50 mmol) were placed. The flaskwas evacuated and backfilled with Ar. To the mixture, an ultrapure water (0.5 mL),trifluoroacetic acid (57.5 μL, 0.75 mmol), and 30% H2O2 (77 μL, 0.75 mmol) wereadded. The mixture was stirred at 25 °C under Ar, followed by treatment with 1:1mixture of saturated Na2S2O3 aqueous solution and saturated NaHCO3 aqueous solution,and extraction with ether. The organic layer was dried over Na2SO4, filtered, andevaporated. 1,3,5-Trimethoxybenzene or hexamethylbenzene was added as an internalstandard, and 1H NMR analysis was performed to determine a NMR yield. Spectral dataof the products were identical with those of commercially available and authenticsamples.

Reference： [1]Kikushima, Kotaro; Moriuchi, Toshiyuki; Hirao, Toshikazu [Tetrahedron Letters, 2010, vol. 51, # 2, p. 340 - 342]
[2]Location in patent: experimental part Kikushima, Kotaro; Moriuchi, Toshiyuki; Hirao, Toshikazu [Tetrahedron, 2010, vol. 66, # 34, p. 6906 - 6911]
[3]Location in patent: scheme or table Kikushima, Kotaro; Moriuchi, Toshiyuki; Hirao, Toshikazu [Chemistry - An Asian Journal, 2009, vol. 4, # 8, p. 1213 - 1216]
[4]Moriuchi, Toshiyuki; Fukui, Yasuhiro; Sakuramoto, Takashi; Hirao, Toshikazu [Chemistry Letters, 2017, vol. 46, # 12, p. 1708 - 1710]

65
[ 1218988-38-5 ]
[ 16356-02-8 ]
[ 1218988-39-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With Wender's catalyst In 1,2-dichloro-ethane at 20 - 25℃; for 48h; Inert atmosphere;
90%	With silver(I) hexafluorophosphate; dichlorobis(η-4-dibenzo[a,e]cyclooctatetraene)diiridium In 2,2,2-trifluoroethanol; 1,2-dichloro-ethane at 20 - 25℃; for 0.333333h;

Reference： [1]Wender, Paul A.; Sirois, Lauren E.; Stemmler, Rene T.; Williams, Travis J. [Organic Letters, 2010, vol. 12, # 7, p. 1604 - 1607]
[2]Melcher, Michaela-Christina; Von Wachenfeldt, Henrik; Sundin, Anders; Strand, Daniel [Chemistry - A European Journal, 2015, vol. 21, # 2, p. 531 - 535]

66
[ 142-29-0 ]
[ 16356-02-8 ]
[ 1219009-79-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane at 20℃; for 16h; Inert atmosphere; chemoselective reaction;

Reference： [1]Hilt, Gerhard; Paul, Anna; Treutwein, Jonas [Organic Letters, 2010, vol. 12, # 7, p. 1536 - 1539]

67
[ 62303-05-3 ]
[ 16356-02-8 ]
[ 1236228-48-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II); triethylamine; zinc In acetonitrile at 80℃; Inert atmosphere;
86%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine In acetonitrile at 40℃; for 6h; Inert atmosphere; Schlenk technique;

Reference： [1]Liu, Chuan-Che; Parthasarathy, Kanniyappan; Cheng, Chien-Hong [Organic Letters, 2010, vol. 12, # 15, p. 3518 - 3521]
[2]Weng, Wei-Zhi; Xie, Jian; Zhang, Bo [Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3983 - 3988]

68
[ 73183-34-3 ]
[ 16356-02-8 ]
[ 1356497-11-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine)platinum⁽⁰⁾ In N,N-dimethyl-formamide at 80℃; for 3.5h;
45%	With gold In toluene at 100℃; for 72h; Green chemistry; diastereoselective reaction;

Reference： [1]Yoshida, Hiroto; Kawashima, Shota; Takemoto, Yuki; Okada, Kengo; Ohshita, Joji; Takaki, Ken [Angewandte Chemie - International Edition, 2012, vol. 51, # 1, p. 235 - 238]
[2]Chen, Qiang; Zhao, Jian; Ishikawa, Yoshifumi; Asao, Naoki; Yamamoto, Yoshinori; Jin, Tienan [Organic Letters, 2013, vol. 15, # 22, p. 5766 - 5769]

69
[ 566190-87-2 ]
[ 16356-02-8 ]
[ 1361255-89-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With [Rh(dppp)]BF₄ In 1,2-dichloro-ethane at 60℃; for 36h; Inert atmosphere; regioselective reaction;

Reference： [1]Hojo, Daiki; Tanaka, Ken [Organic Letters, 2012, vol. 14, # 6, p. 1492 - 1495]

70
[ 54743-46-3 ]
[ 16356-02-8 ]
1-(6-methoxy-3,4-bis(methoxymethyl)-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With (pentamethylcyclopentadienyl)*Rh(OAc)2; oxygen; copper (I) acetate In tert-Amyl alcohol at 110℃; for 18h;

Reference： [1]Pham, Manh V.; Ye, Baihua; Cramer, Nicolai [Angewandte Chemie - International Edition, 2012, vol. 51, # 42, p. 10610 - 10614,5][Angewandte Chemie, 2012, vol. 124, # 42, p. 10762 - 10766,5] Pham, Manh V.; Ye, Baihua; Cramer, Nicolai [Angewandte Chemie - International Edition, 2012, vol. 51, # 42, p. 10610 - 10614][Angew. Chem., 2012, vol. 124, # 42, p. 10762 - 10766,5]

71
[ 100-69-6 ]
copper(II) tetrafluroborate hexahydrate [ No CAS ]
[ 16356-02-8 ]
3,4-bis(methoxymethyl)quinolizin-5-ium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen In methanol at 60℃; for 18h; Sealed tube;

Reference： [1]Luo, Ching-Zong; Gandeepan, Parthasarathy; Cheng, Chien-Hong [Chemical Communications, 2013, vol. 49, # 76, p. 8528 - 8530]

72
[ 90933-84-9 ]
[ 278603-80-8 ]
[ 16356-02-8 ]
[ 1600513-82-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With Wender's catalyst In 1,2-dichloro-ethane at 20℃; for 19h;	General alkyne dienophile method General procedure: To an oven-dried or flame-dried vial was added 1.1 equiv. TMSBO 2 as a neat liquid followed by 1,2-dichloroethane (DCE, 0.162 M with respect to VCP). To this solution was added 1 equiv. VCP 1 as a neat liquid, and then 2-5 mol% [(naph)Rh(COD)]SbF6 in one portion. The reaction was stirredfor 6 h or until consumption of 1 could be observed by TLC. The second alkyne was then added and the reaction monitored by TLC for consumption of the intermediate diene. The reaction was quenched with dilute acid and the resulting products purified via column chromatography. Results for these substrates are summarized in Table 1.

Reference： [1]Wender, Paul A.; Fournogerakis, Dennis N.; Jeffreys, Matthew S.; Quiroz, Ryan V.; Inagaki, Fuyuhiko; Pfaffenbach, Magnus [Nature Chemistry, 2014, vol. 6, # 5, p. 448 - 452]

73
[ 36122-35-7 ]
[ 16356-02-8 ]
C₁₅H₁₆O₄ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 37138 - 37141

74
[ 278603-80-8 ]
[ 16356-02-8 ]
[ 1218988-37-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 1-(2-methoxyethoxy)-1-vinylcyclopropane; 1,4-dimethoxy-2-butyne With bis(1,5-cyclooctadiene)diiridium(I) dichloride; silver(I) hexafluorophosphate In 2,2,2-trifluoroethanol; 1,2-dichloro-ethane at 20 - 25℃; for 0.0166667h; Stage #2: With hydrogenchloride In ethanol; 2,2,2-trifluoroethanol; water; 1,2-dichloro-ethane; acetone for 0.25h;

Reference： [1]Melcher, Michaela-Christina; Von Wachenfeldt, Henrik; Sundin, Anders; Strand, Daniel [Chemistry - A European Journal, 2015, vol. 21, # 2, p. 531 - 535]

75
[ 74-89-5 ]
[ 1896-62-4 ]
[ 16356-02-8 ]
2,3-bis(methoxymethyl)-1,6-dimethyl-4-phenylpyridin-1-ium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium tetrafluoroborate; [Cp*RhCl₂]2; copper(II) acetate monohydrate In methanol at 80℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Luo, Ching-Zong; Jayakumar, Jayachandran; Gandeepan, Parthasarathy; Wu, Yun-Ching; Cheng, Chien-Hong [Organic Letters, 2015, vol. 17, # 4, p. 924 - 927]

76
[ 100-39-0 ]
[ 16356-02-8 ]
(Z)-1,4-diphenyl-2,3-dimethoxymethylbut-2-ene [ No CAS ]
[ 103-29-7 ]