Aminals as powerful XAT-reagents: activation of fluorinated alkyl chlorides

Aminals as powerful XAT-reagents: activation of fluorinated alkyl chlorides Full article

Journal

Chemical Science
ISSN: 2041-6520 , E-ISSN: 2041-6539

Output data

Year: 2023, Volume: 14, Number: 12, Pages: 3229-3234 Pages count : 6 DOI: 10.1039/d3sc00027c

Authors

Kostromitin Vladislav S. ^1,2 , Sorokin Artem O. ^1,2 , Levin Vitalij V. ² , Dilman Alexander D. ²

Affiliations

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

Readily available 1,3,5-trimethyl-1,3,5-triazinane serves as an efficient reagent for halogen atom transfer. Under photocatalytic conditions, the triazinane generates an α-aminoalkyl radical, which can activate the C–Cl bond of fluorinated alkyl chlorides. The hydrofluoroalkylation reaction between fluorinated alkyl chlorides and alkenes is described. The efficiency of the diamino-substituted radical derived from the triazinane is associated with stereoelectronic effects defined by a six-membered cycle forcing the anti-periplanar arrangement of the radical orbital and lone pairs of adjacent nitrogen atoms.

Kostromitin V.S. , Sorokin A.O. , Levin V.V. , Dilman A.D.
Aminals as powerful XAT-reagents: activation of fluorinated alkyl chlorides
Chemical Science. 2023. V.14. N12. P.3229-3234. DOI: 10.1039/d3sc00027c WOS Scopus OpenAlex

Web of science:	WOS:000939898400001
Scopus:	2-s2.0-85149507072
OpenAlex:	W4321454938

DB	Citing
OpenAlex	24
Scopus	21
Web of science	16