Cu-Catalyzed Asymmetric Hydrogermylation Towards C- and Ge-Stereogenic Germanes

Lin, Weidong1,2; Ren, Li-Qing1,2; Du Chen, Cadmus1,2; Han, Xue1,2; Zhang, Lu1,2; Chen, Zihao1,2; Guo, Jiandong1,3; He, Chuan2

2024-06-01

10.31635/ccschem.024.202404335

CCS CHEMISTRY   影响因子和分区

2096-5745

Organogermanium compounds have exhibited great application potential in the fields of synthetic chemistry, materials science, and medicinal chemistry due to their unique chemical, physical, and biological properties. In this regard, the development of effective methods for the synthesis of these compounds has attracted increased attention. Among various approaches, hydrogermylation of unsaturated carbon-carbon bonds stands out for its directness and atom economy. However, catalytic asymmetric hydrogermylation methods to assemble diverse chiral germanes remain a challenge to chemical synthesis. Herein, we report the development of a Cu-catalyzed asymmetric intermolecular hydrogermylation of simple activated alkenes with hydrogermanes, which allows for the efficient and straightforward construction of enantioenriched carbon- and germaniumstereogenic germanes in decent yields with good to excellent enantioselectivities under mild conditions. Central to the success is the ligand-steered in -situ generation of a key [Cu-Ge] species, followed by the enantioselective insertion of alkenes, delivering chiral organogermanes with precise chemo-, regio-, and stereocontrol. This facile and convenient approach towards versatile chiral germane platform molecules promises to unlock novel applications across a range of fields.

asymmetric catalysis copper catalysis enantioselective hydrogermylation chiral germanes Ge-stereogenic chirality

ESCI

英语

第一 ; 通讯

National Natural Science Foundation of China["22122102","22101120","22271134","22203070"] ; Guang-dong Provincial Key Laboratory of Catalysis[2020B121201002] ; Guangdong Pearl River Talent Pro-gram[2019QN01Y628] ; Shenzhen Science and Technology Innovation Committee["RCJC20221008092723013","JCYJ202308070931040 09"]

Chemistry

Chemistry, Multidisciplinary

WOS:001258104800001

CHINESE CHEMICAL SOC

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
3.Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China

Lin, Weidong,Ren, Li-Qing,Du Chen, Cadmus,et al. Cu-Catalyzed Asymmetric Hydrogermylation Towards C- and Ge-Stereogenic Germanes[J]. CCS CHEMISTRY,2024.

Lin, Weidong.,Ren, Li-Qing.,Du Chen, Cadmus.,Han, Xue.,Zhang, Lu.,...&He, Chuan.(2024).Cu-Catalyzed Asymmetric Hydrogermylation Towards C- and Ge-Stereogenic Germanes.CCS CHEMISTRY.

Lin, Weidong,et al."Cu-Catalyzed Asymmetric Hydrogermylation Towards C- and Ge-Stereogenic Germanes".CCS CHEMISTRY (2024).