Modular access to alkylgermanes via reductive germylative alkylation of activated olefins under nickel catalysis

Rui Gu, Xiujuan Feng, Ming Bao () and Xuan Zhang ()
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Rui Gu: Nanjing University of Information Science and Technology
Xiujuan Feng: Dalian University of Technology
Ming Bao: Dalian University of Technology
Xuan Zhang: Nanjing University of Information Science and Technology

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Carbon-introducing difunctionalization of C-C double bonds enabled by transition-metal catalysis is one of most straightforward and efficient strategies to construct C-C and C-X bonds concurrently from readily available feedstocks towards structurally diverse molecules in one step; however, analogous difunctionalization for introducing germanium group and other functionalities remains elusive. Herein, we describe a nickel-catalyzed germylative alkylation of activated olefins with easily accessible primary, secondary and tertiary alkyl bromides and chlorogermanes as the electrophiles to form C-Ge and C-Calkyl bonds simultaneously. This method provides a modular and facile approach for the synthesis of a broad range of alkylgermanes with good functional group compatibility, and can be further applied to the late-stage modification of natural products and pharmaceuticals, as well as ligation of drug fragments. More importantly, this platform enables the expedient synthesis of germanium substituted ospemifene-Ge-OH, which shows improved properties compared to ospemifene in the treatment of breast cancer cells, demonstrating high potential of our protocol in drug development.

Date: 2023
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DOI: 10.1038/s41467-023-43561-z

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