Orchestrating a β-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols Using Organoboron Reagents

Thangeswaran Ramar, Murugaiah A. M. Subbaiah* and Andivelu Ilangovan*

*Biocon BMS R&D Centre, Biocon Park, Bangalore 560099; Bharathidasan University, Palkalaiperur, Thiruchirapalli 620024, India, Email: murugaiah.andappansyngeneintl.com, ilangovanbdu.ac.in

T. Ramar, M. A. M. Subbaiah, A. Ilangovan, J. Org. Chem., 2022, 87, 4508-4523.

DOI: 10.1021/acs.joc.1c02735

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Abstract

An arylation/alkenylation of homoenolates from cyclopropanol precursors with boronic acids provides β-substituted enone and dienone derivatives in good yields. A simple ligand-free Pd(II) catalytic system is most efficient under open air conditions. The reaction tolerates a wide range of substrates and a variety of functional groups.

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proposed mechanism

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Utility of Organoboron Reagents in Arylation of Cyclopropanols via Chelated Pd(II) Catalysis: Chemoselective Access to β-Aryl Ketones

T. Ramar, M. A. M. Subbaiah, A. Ilangovan, J. Org. Chem., 2020, 85, 7711-7727.

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Key Words

substituted enones, copper compounds

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ID: J42-Y2022