Dinuclear gold-catalyzed divergent dechlorinative radical borylation of gem-dichloroalkanes

Cheng-Long Ji, Hongliang Chen, Qi Gao, Jie Han, Weipeng Li and Jin Xie ()
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Cheng-Long Ji: Nanjing University
Hongliang Chen: Nanjing University
Qi Gao: Nanjing University
Jie Han: Nanjing University
Weipeng Li: Nanjing University
Jin Xie: Nanjing University

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract The enormous and widespread use of organoboronic acids has prompted the development of innovative synthetic methodologies to meet the demands on structural diversity and functional group tolerance. The existing photoinduced defunctionalization radical borylation, typically focused on the conversion of one C-X bond (X= Br, I, or other leaving group) into only one C-B bond. Herein, we disclose a divergent radical dechloroborylation reaction enabled by dinuclear gold catalysis with visible light irradiation. A wide range of structurally diverse alkyl boronic, α-chloroboronic, and gem-diboronic esters can be synthesized in moderate to good yields (up to 92%). Its synthetic robustness is further demonstrated on a preparative scale and applied to late-stage diversification of complex molecules. The process hinges on a C-Cl bond relay activation in readily available gem-dichloroalkanes through inner-sphere electron transfer, overcoming the redox potential limits of unreactive alkyl chlorides.

Date: 2024
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DOI: 10.1038/s41467-024-48085-8

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