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

51 Citations (Scopus)

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.
LanguageEnglish
Number of pages33
JournalJournal of Organic Chemistry
Early online date5 Apr 2016
DOIs
Publication statusE-pub ahead of print - 5 Apr 2016

Fingerprint

Boronic Acids
Amination
Amines
Esters

Keywords

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

Cite this

Vantourout, Julien C. ; Law, Robert P. ; Isidro-Llobet, Albert ; Atkinson, Stephen J. ; Watson, Allan J. B. / Chan–Evans–Lam amination of boronic acid pinacol (BPin) esters : overcoming the aryl amine problem. In: Journal of Organic Chemistry. 2016.
@article{85251d060af74df680a28d05b279302d,
title = "Chan–Evans–Lam amination of boronic acid pinacol (BPin) esters: overcoming the aryl amine problem",
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.",
keywords = "Chan-Evans-Lam, boronic acid pinacol, BPin, esters, aryl, alkyl, amines",
author = "Vantourout, {Julien C.} and Law, {Robert P.} and Albert Isidro-Llobet and Atkinson, {Stephen J.} and Watson, {Allan J. B.}",
year = "2016",
month = "4",
day = "5",
doi = "10.1021/acs.joc.6b00466",
language = "English",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",

}

Chan–Evans–Lam amination of boronic acid pinacol (BPin) esters : overcoming the aryl amine problem. / Vantourout, Julien C.; Law, Robert P.; Isidro-Llobet, Albert; Atkinson, Stephen J.; Watson, Allan J. B.

In: Journal of Organic Chemistry, 05.04.2016.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Chan–Evans–Lam amination of boronic acid pinacol (BPin) esters

T2 - Journal of Organic Chemistry

AU - Vantourout, Julien C.

AU - Law, Robert P.

AU - Isidro-Llobet, Albert

AU - Atkinson, Stephen J.

AU - Watson, Allan J. B.

PY - 2016/4/5

Y1 - 2016/4/5

N2 - 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.

AB - 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.

KW - Chan-Evans-Lam

KW - boronic acid pinacol

KW - BPin

KW - esters

KW - aryl

KW - alkyl

KW - amines

UR - http://pubs.acs.org/loi/joceah

U2 - 10.1021/acs.joc.6b00466

DO - 10.1021/acs.joc.6b00466

M3 - Article

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -