Synthesis of gem-Difluorinated N-Boc Amines from N-Boc Imines via Difluorinated Phosphonium Salts

Synthesis of gem-Difluorinated N-Boc Amines from N-Boc Imines via Difluorinated Phosphonium Salts Full article

Journal

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

Output data

Year: 2025, Volume: 90, Number: 28, Pages: 10148-10153 Pages count : 6 DOI: 10.1021/acs.joc.5c01356

Authors

Lozhkin Gregory A. ^1,2 , Trifonov Alexey L. ² , Dilman Alexander D. ²

Affiliations

1	Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Leninskie Gory 1–3, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky Prospekt 47, Russian Federation

A one-pot metal-free protocol toward gem-difluorinated N-Boc-protected amines is described. At first, N-Boc imines react with in situ-generated phosphorus ylide, producing gem-difluorinated phosphonium salts, which subsequently behave as a source of difluoroalkyl radicals under photoredox conditions. The process works using a phenothiazine-type photocatalyst, Hantzsch ester, and electron-deficient alkenes. Facile removal of the Boc group from the products affords difluorinated primary amine hydrochlorides.

Lozhkin G.A. , Trifonov A.L. , Dilman A.D.
Synthesis of gem-Difluorinated N-Boc Amines from N-Boc Imines via Difluorinated Phosphonium Salts
Journal of Organic Chemistry. 2025. V.90. N28. P.10148-10153. DOI: 10.1021/acs.joc.5c01356 WOS OpenAlex

Web of science:	WOS:001526000000001
OpenAlex:	W4412128422

Пока нет цитирований