Organocalcium-Complex-Catalyzed Dehydrogenative Silylation and Mono/Dihydrosilylation Tandem Reactions of Terminal Alkynes

被引：7

作者：

Li, Tao ^{[1
]}

Liu, Ruixin ^{[1
]}

Liu, Xiaojuan ^{[1
]}

Chen, Yaofeng ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] South China Univ Technol, Spin X Inst, Sch Chem & Chem Engn, State Key Lab Luminescent Mat & Devices,Guangdong, Guangzhou 510641, Peoples R China

来源：

ORGANIC LETTERS | 2023年

基金：

中国国家自然科学基金;

关键词：

INTRAMOLECULAR HYDROAMINATION; COUPLING REACTIONS; CALCIUM; HYDROSILYLATION; ALKENES; REAGENTS; AMINES; HYDROSILANES; REACTIVITY; SILANES;

D O I：

10.1021/acs.orglett.2c04230

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In principle, catalytic dehydrogenative silylation and mono/dihydrosilylation tandem reactions of terminal alkynes with hydrosilanes provide gem-disilylated alkenes or gem-trisilylated alkanes, but very little progress has been made. Herein, we report organo-calcium-complex-catalyzed dehydrogenative silylation and mono/ dihydrosilylation tandem reactions of terminal alkynes with hydro-silanes in one pot, which produce gem-disilylated alkenes in moderate yields and gem-trisilylated alkanes in high yields. We also briefly demonstrate that the synthesized gem-disilylated alkenes can be easily transformed into other organosilanes.

引用

页码：761 / 765

页数：5

共 49 条

[1] Calcium-mediated hydrophosphination of diphenylethyne and diphenylbutadiyne as well as crystal structure of 1,4-diphenyl-1,4-bis(diphenylphosphanyl)buta-1,3-diene [J].

Al-Shboul, Tareq M. A. ;

Goerls, Helmar ;

Westerhausen, Matthias .

INORGANIC CHEMISTRY COMMUNICATIONS, 2008, 11 (12) :1419-1421

[2] Imine hydrogenation with simple alkaline earth metal catalysts [J].

Bauer, Heiko ;

Alonso, Mercedes ;

Farber, Christian ;

Elsen, Holger ;

Pahl, Jurgen ;

Causero, Andrea ;

Ballmann, Gerd ;

De Proft, Frank ;

Harder, Sjoerd .

NATURE CATALYSIS, 2018, 1 (01) :40-47

[3]

Brook M. A., 2000, SILICON ORGANIC ORGA

[4] Hydrosilylation of alkenes with early main-group metal catalysts [J].

Buch, F ;

Brettar, H ;

Harder, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) :2741-2745

[5] A study on chiral organocalcium complexes: Attempts in enantioselective catalytic hydrosilylation and intramolecular hydroamination of alkenes [J].

Buch, Frank ;

Harder, Sjoerd .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2008, 63 (02) :169-177

[6] The azametallacyclopropane Ca(η2-Ph2CNPh)(hmpa)3:: A calcium alternative to a versatile Ytterbium(II) catalyst [J].

Buch, Frank ;

Harder, Sjoerd .

ORGANOMETALLICS, 2007, 26 (21) :5132-5135

[7] Recent Advances in Hydrometallation of Alkenes and Alkynes via the First Row Transition Metal Catalysis [J].

Chen, Jianhui ;

Guo, Jun ;

Lu, Zhan .

CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (11) :1075-1109

[8] Catalytic Selective Dihydrosilylation of Internal Alkynes Enabled by Rare-Earth Ate Complex [J].

Chen, Wufeng ;

Song, Haibin ;

Li, Jianfeng ;

Cui, Chunming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (06) :2365-2369

[9]

Cheng Z., 2023, ANGEW CHEM INT EDIT, V62

[10] Intramolecular Hydroamination of Aminoalkenes by Calcium and Magnesium Complexes: A Synthetic and Mechanistic Study [J].

Crimmin, Mark R. ;

Arrowsmith, Merle ;

Barrett, Anthony G. M. ;

Casely, Ian J. ;

Hill, Michael S. ;

Procopiou, Panayiotis A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (28) :9670-9685

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