Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity
2
Publication type: Journal Article
Publication date: 2017-03-24
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
28266843
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.
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315
Total citations:
315
Citations from 2025:
31
(9.84%)
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Vantourout J. C. et al. Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity // Journal of the American Chemical Society. 2017. Vol. 139. No. 13. pp. 4769-4779.
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Vantourout J. C., Miras H., Isidro-Llobet A., Sproules S., Watson A. J. B. Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity // Journal of the American Chemical Society. 2017. Vol. 139. No. 13. pp. 4769-4779.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jacs.6b12800
UR - https://doi.org/10.1021/jacs.6b12800
TI - Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity
T2 - Journal of the American Chemical Society
AU - Vantourout, Julien C
AU - Miras, H.
AU - Isidro-Llobet, Albert
AU - Sproules, Stephen
AU - Watson, Allan J. B.
PY - 2017
DA - 2017/03/24
PB - American Chemical Society (ACS)
SP - 4769-4779
IS - 13
VL - 139
PMID - 28266843
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (up to 50 authors)
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@article{2017_Vantourout,
author = {Julien C Vantourout and H. Miras and Albert Isidro-Llobet and Stephen Sproules and Allan J. B. Watson},
title = {Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity},
journal = {Journal of the American Chemical Society},
year = {2017},
volume = {139},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jacs.6b12800},
number = {13},
pages = {4769--4779},
doi = {10.1021/jacs.6b12800}
}
Cite this
MLA
Copy
Vantourout, Julien C., et al. “Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity.” Journal of the American Chemical Society, vol. 139, no. 13, Mar. 2017, pp. 4769-4779. https://doi.org/10.1021/jacs.6b12800.
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