Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
Тип публикации: Journal Article
Дата публикации: 2016-04-18
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
27045570
Organic Chemistry
Краткое описание
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.
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Vantourout J. C. et al. Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem // Journal of Organic Chemistry. 2016. Vol. 81. No. 9. pp. 3942-3950.
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Vantourout J. C., Law R. P., Isidro-Llobet A., Atkinson S. J., Watson A. J. B. Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem // Journal of Organic Chemistry. 2016. Vol. 81. No. 9. pp. 3942-3950.
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TY - JOUR
DO - 10.1021/acs.joc.6b00466
UR - https://doi.org/10.1021/acs.joc.6b00466
TI - Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
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
DA - 2016/04/18
PB - American Chemical Society (ACS)
SP - 3942-3950
IS - 9
VL - 81
PMID - 27045570
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2016_Vantourout,
author = {Julien C Vantourout and Robert P Law and Albert Isidro-Llobet and Stephen J Atkinson and Allan J. B. Watson},
title = {Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.joc.6b00466},
number = {9},
pages = {3942--3950},
doi = {10.1021/acs.joc.6b00466}
}
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MLA
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Vantourout, Julien C., et al. “Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem.” Journal of Organic Chemistry, vol. 81, no. 9, Apr. 2016, pp. 3942-3950. https://doi.org/10.1021/acs.joc.6b00466.