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Scope and Mechanism in Palladium-Catalyzed Isomerizations of Highly Substituted Allylic, Homoallylic, and Alkenyl Alcohols

Evgeny Larionov, Luqing Lin, Laure Guénée and Clément Mazet*

*Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Geneva, Switzerland, Email: clement.mazetunige.ch

E. Larionov, L. Lin, L. Guénée, C. Mazet, J. Am. Chem. Soc., 2014, 136, 16882-16894.

DOI: 10.1021/ja508736u (free Supporting Information)


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Abstract

An operationally simple palladium-catalyzed isomerization of highly substituted allylic alcohols and alkenyl alcohols is applicable to a broad range of substrates and displays a wide functional group tolerance. Carbonyl compounds can usually be isolated in high chemical yield. Experimental and computational mechanistic investigations provide evidence for a chain-walking process consisting of repeated migratory insertion/β-H elimination sequences.

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Key Words

ketones, aldehydes


ID: J48-Y2014