Orthogonal sp3‐Ge/B Bimetallic Modules: Enantioselective Construction and Enantiospecific Cross‐Coupling

Author:

Xu Meng‐Yu1,Jiang Wei‐Tao2,Xia Ming‐Zhi1,An Zi‐Long2,Xie Xiu‐Ying2,Xiao Bin2ORCID

Affiliation:

1. Key Laboratory of Green and Precise Synthetic Chemistry and Applications Ministry of Education Huaibei Normal University Huaibei, Anhui 235000 P. R. China

2. Department of Chemistry University of Science and Technology of China Hefei 230026 China

Abstract

AbstractIn this study, a series of enantioenriched sp3‐Ge/B bimetallic modules were successfully synthesized via an enantioselective copper‐catalyzed hydroboration of carbagermatrane (Ge)‐containing alkenes. Orthogonal cross‐coupling selectivity under different Pd‐catalyzed conditions was achieved in an enantiospecific manner. Notably, the chiral secondary Ge exhibited a remarkable transmetallation ability prior to primary or secondary Bpin. The effectiveness of this Ge/B bimetallic strategy was further demonstrated through the development of new functional small molecules with Aggregation‐Induced Emission (AIE) and Circularly Polarized Luminescence (CPL) performance. This represents the first successful example of synthesis of enantioenriched alkylgermanium reagents that permit enantiospecific cross‐coupling reactions.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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