volume 84 issue 17 pages 11068-11079

Light mediated dual phosphine/copper catalyzed atom transfer radical addition reaction.

Publication typeJournal Article
Publication date2019-08-14
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
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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GOST Copy
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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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.