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Remote Migratory Cross-Electrophile Coupling and Olefin Hydroarylation Reactions Enabled by in Situ Generation of NiH

Fenglin Chen, Ke Chen, Yao Zhang, Yuli He, Yi-Ming Wang* and Shaolin Zhu*

*Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States; School of Chemistry, Nanjing University, Nanjing 210093, China, Email: ym.wangpitt.edu, shaolinzhunju.edu.cn

F. Chen, K. Chen, Y. Zhang, Y. He, Y.-M. Wang, S. Zhu, J. Am. Chem. Soc., 2017, 139, 13929-13935.

DOI: 10.1021/jacs.7b08064 (free Supporting Information)


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Abstract

A ligand-controlled nickel migration/arylation enables a highly efficient remote reductive cross-electrophile coupling. This general protocol allows the use of abundant and bench-stable alkyl bromides and aryl bromides for the synthesis of a wide range of structurally diverse 1,1-diarylalkanes in excellent yields and high regioselectivities under mild conditions.

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proposed mechanism



Key Words

1,1-diarylalkanes, manganese


ID: J48-Y2017