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

doi:10.1021/acs.joc.6b00466

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

Pure And Applied Chemistry

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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 language	English
Number of pages	33
Journal	Journal of Organic Chemistry
Early online date	5 Apr 2016
DOIs	https://doi.org/10.1021/acs.joc.6b00466
Publication status	E-pub ahead of print - 5 Apr 2016

Keywords

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

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10.1021/acs.joc.6b00466

Vantourout-etal-JOC-2016-Chan–evans–lam-amination-of-boronic-acid-pinacol-bpin-estersAccepted author manuscript, 583 KB

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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",

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doi = "10.1021/acs.joc.6b00466",

language = "English",

journal = "Journal of Organic Chemistry",

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

T2 - overcoming the aryl amine problem

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

SN - 0022-3263

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

Chan–Evans–Lam amination of boronic acid pinacol (BPin) esters: overcoming the aryl amine problem

Abstract

Keywords

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