Streamlined Construction of Silicon-Stereogenic Silanes by Tandem Enantioselective C-H Silylation/Alkene Hydrosilylation

Mu, Delong1,2; Yuan, Wei1,2; Chen, Shuyou1,2; Wang, Na1,2; Yang, Bo1,2; You, Lijun1,2; Zu, Bing1,2; Yu, Peiyuan1,2; He, Chuan1,2

2020-08-05

10.1021/jacs.0c04863

Journal of the American Chemical Society   影响因子和分区

0002-7863

1520-5126

A rhodium-catalyzed tandem enantioselective C-H silylation/alkene hydrosilylation of dihydrosilanes, which enables the streamlined construction of a wide range of silicon-stereogenic silanes, is successfully developed. This process involves a SiH2-steered highly enantioselective C-H silylation to furnish the corresponding desymmetric monohydrosilanes, which are subsequently trapped with alkenes in a stereospecific fashion to build functionally diverse asymmetrically tetrasubstituted silanes. This general strategy combines readily available dihydrosilanes and alkenes to construct various enantioenriched silicon-stereogenic silanes, including 9-silafluorenes, Si-bridged ladder compounds, and benzosilolometallocenes, in a single step with good to excellent yields and enantioselectivities.

CATALYZED ASYMMETRIC-SYNTHESIS DEHYDROGENATIVE SILYLATION ORGANOSILICON COMPOUNDS CHIRALITY TRANSFER CHEMISTRY STEREOCHEMISTRY DIBENZOSILOLES SUBSTITUTION CARBON

SCI ; EI ; IC

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China[21901104] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; China Postdoctoral Science Foundation[2019M651153] ; Shenzhen Clean Energy Research Institute[CERI-KY-2019-003]

Chemistry

Chemistry, Multidisciplinary

WOS:000558793400029

AMER CHEMICAL SOC

20203709150750

Enantioselectivity ; Hydrosilylation ; Silicon ; Silicon compounds

Nonferrous Metals and Alloys excluding Alkali and Alkaline Earth Metals:549.3 ; Physical Chemistry:801.4 ; Organic Compounds:804.1

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

Mu, Delong,Yuan, Wei,Chen, Shuyou,et al. Streamlined Construction of Silicon-Stereogenic Silanes by Tandem Enantioselective C-H Silylation/Alkene Hydrosilylation[J]. Journal of the American Chemical Society,2020,142(31):13459-13468.

Mu, Delong.,Yuan, Wei.,Chen, Shuyou.,Wang, Na.,Yang, Bo.,...&He, Chuan.(2020).Streamlined Construction of Silicon-Stereogenic Silanes by Tandem Enantioselective C-H Silylation/Alkene Hydrosilylation.Journal of the American Chemical Society,142(31),13459-13468.

Mu, Delong,et al."Streamlined Construction of Silicon-Stereogenic Silanes by Tandem Enantioselective C-H Silylation/Alkene Hydrosilylation".Journal of the American Chemical Society 142.31(2020):13459-13468.