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Enantioselective Redox-Relay Oxidative Heck Arylations of Acyclic Alkenyl Alcohols using Boronic Acids

Tian-Sheng Mei, Erik W. Werner, Alexander J. Burckle and Matthew S. Sigman*

*Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States, Email: sigmanchem.utah.edu

T.-S. Mei, E. W. Werner, A. J. Burckle, M. S. Sigman, J. Am. Chem. Soc., 2013, 135, 6830-6833.

DOI: 10.1021/ja402916z (free Supporting Information)


Abstract

A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acids delivers remotely functionalized arylated carbonyl products, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. The regioselectivity of the initial migratory insertion depends on the electronic nature of the boronic acid.

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Key Words

arylation, oxygen, Heck reaction


ID: J48-Y2013