Chiral PSiSi-Ligand Enabled Iridium-Catalyzed Atroposelective Intermolecular C-H Silylation

Yang, Bo1,2; Gao, Jihui1,2; Tan, Xingfa1,2; Ge, Yicong1,2; He, Chuan1,2

2023-07-01

10.1002/anie.202307812

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Catalytic enantioselective intermolecular C-H silylation offers an efficient approach for the rapid construction of chiral organosilicon compounds, but remains a significant challenge. Herein, a new type of chiral silyl ligand is developed, which enables the first iridium-catalyzed atroposelective intermolecular C-H silylation reaction of 2-arylisoquinolines. This protocol features mild reaction conditions, high atom economy, and remarkable yield with excellent stereoselectivity (up to 99 % yield, 99 % ee), delivering enantioenriched axially chiral silane platform molecules with facile convertibility. Key to the success of this unprecedented transformation relies on a novel chiral PSiSi-ligand, which facilitates the intermolecular C-H silylation process with perfect chem-, regio- and stereo-control via a multi-coordinated silyl iridium complex.

Asymmetric Catalysis Axial Chirality Chiral Silyl Ligand C-H Activation Intermolecular Silylation

SCI ; EI ; IC ; CCR

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China["22122102","22101120","22271134"] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Guangdong Pearl River Talent Program[2019QN01Y628] ; Shenzhen Science and Technology Innovation Committee[RCJC20221008092723013]

Chemistry

Chemistry, Multidisciplinary

WOS:001034853600001

WILEY-V C H VERLAG GMBH

20233114460475

Catalysis ; Iridium compounds ; Silicon compounds ; Stereochemistry

Chemistry:801 ; 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, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China

Yang, Bo,Gao, Jihui,Tan, Xingfa,et al. Chiral PSiSi-Ligand Enabled Iridium-Catalyzed Atroposelective Intermolecular C-H Silylation[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62(36).

Yang, Bo,Gao, Jihui,Tan, Xingfa,Ge, Yicong,&He, Chuan.(2023).Chiral PSiSi-Ligand Enabled Iridium-Catalyzed Atroposelective Intermolecular C-H Silylation.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62(36).

Yang, Bo,et al."Chiral PSiSi-Ligand Enabled Iridium-Catalyzed Atroposelective Intermolecular C-H Silylation".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62.36(2023).