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Catalytic Regioselective Olefin Hydroarylation(alkenylation) by Sequential Carbonickelation-Hydride Transfer

Chen-Fei Liu, Xiaohua Luo, Hongyu Wang* and Ming Joo Koh*

*Department of Chemistry, National University of Singapore, 4 Science Drive 2, Singapore, 117544, Republic of Singapore, Email: chmwhonus.edu.sg, chmkmjnus.edu.sg

C.-F. Liu, X. Luo, H. Wang, M. J. Koh, J. Am. Chem. Soc., 2021, 143, 9498-9506.

DOI: 10.1021/jacs.1c03228 (free Supporting Information)


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Abstract

A dimeric Ni(I) catalyst and an exogenous alkoxide base promote Markovnikov-selective hydroarylation (alkenylation) of unactivated and activated olefins using organo bromides or triflates derived from widely available phenols and ketones. Products bearing aryl- and alkenyl-substituted tertiary and quaternary centers could be isolated in very good yield and excellent regioisomeric ratios.

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proposed mechanism



Key Words

arylation, isopropanol


ID: J48-Y2021