Light mediated dual phosphine/copper catalyzed atom transfer radical addition reaction.
Publication type: Journal Article
Publication date: 2019-08-14
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31409063
Organic Chemistry
Abstract
The atom transfer radical addition reaction catalyzed by triphenylphosphine and copper(I) halide is described. The reaction proceeds under irradiation with 365 nm light using a light emitting diode, and performed in a regular glassware. The proposed mechanism involves the formation of quaternary phosphonium salt, which undergoes single electron reduction by the copper(I) salt via photoinduced electron transfer. The method works well for terminal alkenes and activated organic halides such as esters of bromo- and iodoacetic acid and bromoacetonitrile. gem-Difluorinated styrenes, for which atom transfer reactions are rare, also proved to be good substrates for this phosphine/copper catalyzed protocol.
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38
Total citations:
38
Citations from 2024:
13
(34.21%)
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GOST
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Fedorov O. V. et al. Light mediated dual phosphine/copper catalyzed atom transfer radical addition reaction. // Journal of Organic Chemistry. 2019. Vol. 84. No. 17. pp. 11068-11079.
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Fedorov O. V., Scherbinina S. I., Levin V. V., Dilman A. D. Light mediated dual phosphine/copper catalyzed atom transfer radical addition reaction. // Journal of Organic Chemistry. 2019. Vol. 84. No. 17. pp. 11068-11079.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b01649
UR - https://doi.org/10.1021/acs.joc.9b01649
TI - Light mediated dual phosphine/copper catalyzed atom transfer radical addition reaction.
T2 - Journal of Organic Chemistry
AU - Fedorov, Oleg V.
AU - Scherbinina, Sofya I
AU - Levin, Vitalij V
AU - Dilman, Alexander D
PY - 2019
DA - 2019/08/14
PB - American Chemical Society (ACS)
SP - 11068-11079
IS - 17
VL - 84
PMID - 31409063
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Fedorov,
author = {Oleg V. Fedorov and Sofya I Scherbinina and Vitalij V Levin and Alexander D Dilman},
title = {Light mediated dual phosphine/copper catalyzed atom transfer radical addition reaction.},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.joc.9b01649},
number = {17},
pages = {11068--11079},
doi = {10.1021/acs.joc.9b01649}
}
Cite this
MLA
Copy
Fedorov, Oleg V., et al. “Light mediated dual phosphine/copper catalyzed atom transfer radical addition reaction..” Journal of Organic Chemistry, vol. 84, no. 17, Aug. 2019, pp. 11068-11079. https://doi.org/10.1021/acs.joc.9b01649.