Enantioselective Intermolecular C-H Silylation of Heteroarenes for the Synthesis of Acyclic Si-Stereogenic Silanes

Chen, Shuyou1,2; Zhu, Jiefeng1,2; Ke, Jie1,2; Li, Yingzi1,2; He, Chuan1,2

2022-03-01

10.1002/anie.202117820

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Intermolecular C-H silylation for the synthesis of acyclic silanes bearing a silicon-stereogenic center in one enantiomeric form remains unknown to date. Herein, we report the first enantioselective intermolecular C-H silylation of heteroarenes for the synthesis of acyclic silicon-stereogenic heteroarylsilanes. This process undergoes a rhodium-catalyzed direct intermolecular dehydrogenative Si-H/C-H cross-coupling, giving access to a variety of acyclic heteroarylated silicon-stereogenic monohydrosilanes, including bis-Si-stereogenic silanes, in decent yields with excellent chemo-, regio-, and stereo-control, which significantly enlarge the chemical space of the optically active silicon-stereogenic monohydrosilanes.

Asymmetric Catalysis Dehydrogenative Coupling Rhodium Silylation Stereogenic Silanes

SCI ; EI

英语

NI期刊

第一 ; 通讯

National Natural Science Foundation of China[21901104,22122102] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Stable Support Plan Program of Shenzhen Natural Science Fund[20200925152450004]

Chemistry

Chemistry, Multidisciplinary

WOS:000769942600001

WILEY-V C H VERLAG GMBH

20221211803242

Enantioselectivity ; Silicon

Nonferrous Metals and Alloys excluding Alkali and Alkaline Earth Metals:549.3 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
2.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

Chen, Shuyou,Zhu, Jiefeng,Ke, Jie,et al. Enantioselective Intermolecular C-H Silylation of Heteroarenes for the Synthesis of Acyclic Si-Stereogenic Silanes[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022,61.

Chen, Shuyou,Zhu, Jiefeng,Ke, Jie,Li, Yingzi,&He, Chuan.(2022).Enantioselective Intermolecular C-H Silylation of Heteroarenes for the Synthesis of Acyclic Si-Stereogenic Silanes.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,61.

Chen, Shuyou,et al."Enantioselective Intermolecular C-H Silylation of Heteroarenes for the Synthesis of Acyclic Si-Stereogenic Silanes".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 61(2022).