Journal of the American Chemical Society, volume 142, issue 6, pages 2766-2770
δ-C–H Mono- and Dihalogenation of Alcohols
Publication type: Journal Article
Publication date: 2020-01-30
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Alkoxy radicals have long been known to enable remote C-H functionalization via 1,5-hydrogen atom abstraction. However, methods for their generation traditionally have relied upon highly oxidizing metals, ultraviolet radiation, or preformed peroxide intermediates, which has prevented the development of many desirable transformations. Herein we report a new bench-stable precursor that decomposes to free alkoxy radicals via a previously unreported single-electron oxidation pathway. This new precursor enables the fluorination and chlorination of remote C-H bonds under exceptionally mild conditions with exceedingly high monoselectivity. Iterative use of this precursor enables the introduction of a second halogen atom, granting access to remote dihalide motifs, including CF2 and CFCl.
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Citations by publishers
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30 publications, 42.25%
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1 publication, 1.41%
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1 publication, 1.41%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Herron A. N. et al. δ-C–H Mono- and Dihalogenation of Alcohols // Journal of the American Chemical Society. 2020. Vol. 142. No. 6. pp. 2766-2770.
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Herron A. N., Liu D., Xia G., Yu J. δ-C–H Mono- and Dihalogenation of Alcohols // Journal of the American Chemical Society. 2020. Vol. 142. No. 6. pp. 2766-2770.
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TY - JOUR
DO - 10.1021/jacs.9b13171
UR - https://doi.org/10.1021/jacs.9b13171
TI - δ-C–H Mono- and Dihalogenation of Alcohols
T2 - Journal of the American Chemical Society
AU - Liu, Dongxin
AU - Xia, Guoqin
AU - Herron, Alastair N
AU - Yu, Jinquan
PY - 2020
DA - 2020/01/30 00:00:00
PB - American Chemical Society (ACS)
SP - 2766-2770
IS - 6
VL - 142
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2020_Herron,
author = {Dongxin Liu and Guoqin Xia and Alastair N Herron and Jinquan Yu},
title = {δ-C–H Mono- and Dihalogenation of Alcohols},
journal = {Journal of the American Chemical Society},
year = {2020},
volume = {142},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/jacs.9b13171},
number = {6},
pages = {2766--2770},
doi = {10.1021/jacs.9b13171}
}
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Herron, Alastair N., et al. “δ-C–H Mono- and Dihalogenation of Alcohols.” Journal of the American Chemical Society, vol. 142, no. 6, Jan. 2020, pp. 2766-2770. https://doi.org/10.1021/jacs.9b13171.