Journal of the American Chemical Society, volume 139, issue 30, pages 10204-10207
Directed β C–H Amination of Alcohols via Radical Relay Chaperones
Publication type: Journal Article
Publication date: 2017-07-25
Q1
Q1
SJR: 5.489
CiteScore: 24.4
Impact factor: 14.4
ISSN: 00027863, 15205126
PubMed ID:
28741940
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.
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Wappes E. A., Nakafuku K. M., Nagib D. A. Directed β C–H Amination of Alcohols via Radical Relay Chaperones // Journal of the American Chemical Society. 2017. Vol. 139. No. 30. pp. 10204-10207.
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Wappes E. A., Nakafuku K. M., Nagib D. A. Directed β C–H Amination of Alcohols via Radical Relay Chaperones // Journal of the American Chemical Society. 2017. Vol. 139. No. 30. pp. 10204-10207.
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TY - JOUR
DO - 10.1021/jacs.7b05214
UR - https://doi.org/10.1021/jacs.7b05214
TI - Directed β C–H Amination of Alcohols via Radical Relay Chaperones
T2 - Journal of the American Chemical Society
AU - Wappes, Ethan A.
AU - Nakafuku, Kohki M
AU - Nagib, David A
PY - 2017
DA - 2017/07/25
PB - American Chemical Society (ACS)
SP - 10204-10207
IS - 30
VL - 139
PMID - 28741940
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (up to 50 authors)
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@article{2017_Wappes,
author = {Ethan A. Wappes and Kohki M Nakafuku and David A Nagib},
title = {Directed β C–H Amination of Alcohols via Radical Relay Chaperones},
journal = {Journal of the American Chemical Society},
year = {2017},
volume = {139},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jacs.7b05214},
number = {30},
pages = {10204--10207},
doi = {10.1021/jacs.7b05214}
}
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Wappes, Ethan A., et al. “Directed β C–H Amination of Alcohols via Radical Relay Chaperones.” Journal of the American Chemical Society, vol. 139, no. 30, Jul. 2017, pp. 10204-10207. https://doi.org/10.1021/jacs.7b05214.