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Cobalt-Catalyzed 1,1-Diboration of Terminal Alkynes: Scope, Mechanism, and Synthetic Applications

Simon Krautwald, Máté J. Bezdek and Paul J. Chirik*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: pchirikprinceton.edu

S. Krautwald, M. J. Bezdek, P. J. Chirik, J. Am. Chem. Soc., 2017, 139, 3868-3875.

DOI: 10.1021/jacs.7b00445 (free Supporting Information)


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Abstract

A cobalt-catalyzed method for the diboration of terminal alkynes with B2Pin2 proceeds efficiently at 23°C with excellent 1,1-selectivity and broad functional group tolerance. With the unsymmetrical diboron reagent PinB-BDan, stereoselective 1,1-diboration provided products with two boron substituents that exhibit differential reactivity.

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Key Words

vinylboronates


ID: J48-Y2017