Phosphorus(III)-assisted regioselective C–H silylation of heteroarenes

Dingyi Wang; Xiangyang Chen; Jonathan J. Wong; Liqun Jin; Mingjie Li; Yue Zhao; K. N. Houk; Zhuangzhi Shi

doi:10.1038/s41467-020-20531-3

Nature Communications (Jan 2021)

Phosphorus(III)-assisted regioselective C–H silylation of heteroarenes

Dingyi Wang,
Xiangyang Chen,
Jonathan J. Wong,
Liqun Jin,
Mingjie Li,
Yue Zhao,
K. N. Houk,
Zhuangzhi Shi

Affiliations

Dingyi Wang: State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University
Xiangyang Chen: Department of Chemistry and Biochemistry, University of California, Los Angeles
Jonathan J. Wong: Department of Chemistry and Biochemistry, University of California, Los Angeles
Liqun Jin: College of Chemical Engineering, Zhejiang University of Technology
Mingjie Li: State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University
Yue Zhao: State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University
K. N. Houk: Department of Chemistry and Biochemistry, University of California, Los Angeles
Zhuangzhi Shi: State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University

DOI: https://doi.org/10.1038/s41467-020-20531-3
Journal volume & issue: Vol. 12, no. 1
pp. 1 – 8

Abstract

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Indole C-H silylation preferentially occurs at the C3 and C2 positions, while functionalization of the benzene core (C4-C7 sites) remains challenging. Here, the authors report a regioselective C7-H silylation of indole derivatives assisted by strong coordination of the palladium catalyst with a phosphorus directing group.

Published in Nature Communications

ISSN: 2041-1723 (Online)
Publisher: Nature Portfolio
Country of publisher: United Kingdom
LCC subjects: Science
Website: https://www.nature.com/ncomms/

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