Photoinduced radical alkylation of aldehydes with potassium alkyltrifluoroborates

Photoinduced radical alkylation of aldehydes with potassium alkyltrifluoroborates Full article

Journal

Organic chemistry frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2024, Volume: 11, Number: 14, Pages: 3988-3996 Pages count : 9 DOI: 10.1039/d4qo00741g

Authors

Zhilyaev Kirill A. ^1,2 , Zubkov Mikhail O. ² , Kosobokov Mikhail D. 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

Radical addition to the carbonyl group has attracted long-standing interest in synthetic chemistry as it represents an orthogonal approach to classic electrophilic carbonyl reactivity. Herein we describe a protocol for radical alkylation of aldehydes with commercially available and shelf-stable potassium alkyltrifluoroborates. The formation of a complex between the aldehyde and difluoroalkylborane generated from the trifluoroborate and Lewis acid is believed to be a key factor responsible for the reaction efficiency. The process proceeds under visible light irradiation and does not require the use of a photocatalyst.

Zhilyaev K.A. , Zubkov M.O. , Kosobokov M.D. , Levin V.V. , Dilman A.D.
Photoinduced radical alkylation of aldehydes with potassium alkyltrifluoroborates
Organic chemistry frontiers. 2024. V.11. N14. P.3988-3996. DOI: 10.1039/d4qo00741g WOS Scopus OpenAlex

Web of science:	WOS:001238024400001
Scopus:	2-s2.0-85195407687
OpenAlex:	W4399122127

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OpenAlex	2
Web of science	2