Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers Full article

Journal

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

Output data

Year: 2017, Volume: 82, Number: 24, Pages: 12967-12974 Pages count : 8 DOI: 10.1021/acs.joc.7b02467

Authors

Scherbinina Sofya I. ^1,2 , Fedorov Oleg V. ² , Levin Vitalij V. ² , Kokorekin Vladimir A. ^3,2 , Struchkova Marina I. ² , Dilman Alexander D. ²

Affiliations

1	D. Mendeleev University of Chemical Technology of Russia, Higher Chemical College, Miusskaya sq. 9, 125047 Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
3	I. M. Sechenov First Moscow State Medical University, Trubetskaya st. 8-2, 119991 Moscow, Russian Federation

A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.

Scherbinina S.I. , Fedorov O.V. , Levin V.V. , Kokorekin V.A. , Struchkova M.I. , Dilman A.D.
Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
Journal of Organic Chemistry. 2017. V.82. N24. P.12967-12974. DOI: 10.1021/acs.joc.7b02467 WOS Scopus OpenAlex

Web of science:	WOS:000418392600002
Scopus:	2-s2.0-85037551155
OpenAlex:	W2769057973

DB	Citing
OpenAlex	34
Scopus	32
Web of science	32