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Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

Julien C. Vantourout, Haralampos N. Miras, Albert Isidro-Llobet, Stephen Sproules and Allan J. B. Watson*

*Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, Glasgow G1 1XL, United Kingdom, Email: aw260st-andrews.ac.uk

J. C. Vantourout, H. N. Miras, A. Isidro-Llobet, S. Sproules, A. J. B. Watson, J. Am. Chem. Soc., 2017, 139, 4769-4779.

DOI: 10.1021/jacs.6b12800 (free Supporting Information)



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Abstract

A general catalytic Chan-Lam amination overcomes long-standing and unsolved amine and organoboron limitations. Spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of oxidation/protodeboronation side reactions.


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proposed mechanism of the Chan-Lam Amination



Key Words

Chan-Lam coupling


ID: J48-Y2017