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, Allan J. B. Watson

Research output: Contribution to journalArticle

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Abstract

The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.
Original languageEnglish
Number of pages33
JournalJournal of Organic Chemistry
Early online date5 Apr 2016
DOIs
Publication statusE-pub ahead of print - 5 Apr 2016

Keywords

  • Chan-Evans-Lam
  • boronic acid pinacol
  • BPin
  • esters
  • aryl
  • alkyl
  • amines

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