Light-Mediated Dual Phosphine-/Copper-Catalyzed Atom Transfer Radical Addition Reaction

Light-Mediated Dual Phosphine-/Copper-Catalyzed Atom Transfer Radical Addition Reaction Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 17, Pages: 11068-11079 Pages count : 12 DOI: 10.1021/acs.joc.9b01649

Authors

Fedorov Oleg V. ¹ , Scherbinina Sofya I. ^2,1 , Levin Vitalij V. ¹ , Dilman Alexander D. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
2	Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Moscow, Russian Federation

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 was performed in regular glassware. The proposed mechanism involves the formation of quaternary phosphonium salt, which undergoes single electron reduction by copper(I) salt via photo-induced 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.

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. V.84. N17. P.11068-11079. DOI: 10.1021/acs.joc.9b01649 WOS Scopus OpenAlex

Web of science:	WOS:000485089200051
Scopus:	2-s2.0-85071995856
OpenAlex:	W2967170881

DB	Citing
OpenAlex	34
Scopus	27
Web of science	30