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)
see article for more reactions
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.
see article for more examples