Electrochemically driven regioselective C−H phosphorylation of group 8 metallocenes

Hao Zheng, Chang-Hui Liu, Shi-Yu Guo, Gu-Cheng He, Xiang-Ting Min, Bo-Chao Zhou, Ding-Wei Ji, Yan-Cheng Hu and Qing-An Chen ()
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Hao Zheng: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Chang-Hui Liu: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Shi-Yu Guo: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Gu-Cheng He: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Xiang-Ting Min: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Bo-Chao Zhou: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Ding-Wei Ji: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Yan-Cheng Hu: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Qing-An Chen: Dalian Institute of Chemical Physics, Chinese Academy of Sciences

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract Metallocenes are privileged backbones for synthesis and catalysis. However, the direct dehydrogenative C−H functionalization of unsymmetric metallocenes suffers from reactivity and selectivity issues. Herein, we report an electrochemically driven regioselective C−H phosphorylation of group 8 metallocenes. Mechanistic investigations indicate this dehydrogenative cross coupling occurs through an electrophilic radical substitution of the metallocene with a phosphoryl radical, facilitated by the metallocene itself. This work not only offers an efficient and divergent synthesis of phosphorylated metallocenes, but also provides a guide to interpret the reactivity and regioselectivity for the C−H functionalization of unsymmetric metallocenes.

Date: 2022
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DOI: 10.1038/s41467-022-31178-7

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