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Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem

Julien C. Vantourout, Robert P. Law, Albert Isidro-Llobet, Stephen J. Atkinson and Allan J. B. Watson*

*Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, Glasgow, G1 1XL, U.K., Email: allan.watson.100strath.ac.uk

J. C. Vantourout, R. P. Law, A. Isidro-Llobet, S. J. Atkinson, A. J. B. Watson, J. Org. Chem., 2016, 81, 3942-3950.

DOI: 10.1021/acs.joc.6b00466 (free Supporting Information)



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Abstract

Aryl boronic acid pinacol esters can be difficult coupling partners in Chan-Evans-Lam reactions that often deliver low yields, especially with aryl amines. A mixed MeCN/EtOH solvent system enables an effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.


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Key Words

Chan-Lam coupling


ID: J42-Y2016