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Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate

Robert A. Swyka, William G. Shuler, Brian J. Spinello, Wandi Zhang, Chunling Lan, Michael J. Krische*

*Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States, Email: mkrischemail.utexas.edu

R. A. Swyka, W. G. Shuler, B. J. Spinello, W. Zhang, C. Lan, M. J. Krische, J. Am. Chem. Soc., 2019, 141, 6864-6868.

DOI: 10.1021/jacs.9b03113 (free Supporting Information)


Abstract

Whereas rhodium complexes modified by PtBu2Me catalyze formate-mediated aldehyde-vinyl bromide reductive coupling-redox isomerization to form branched ketones, PPh3 as less strongly coordinating ligand promotes vinyl- to allylrhodium isomerization en route to linear ketones.

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Key Words

ketones


ID: J48-Y2019