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Boron Chelates Derived from N-Acylhydrazones as Radical Acceptors: Photocatalyzed Coupling of Hydrazones with Carboxylic Acids Full article

Journal Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052
Output data Year: 2021, Volume: 23, Number: 22, Pages: 8973-8977 Pages count : 5 DOI: 10.1021/acs.orglett.1c03501
Authors Dmitriev Igor A. 1 , Levin Vitalij V. 1 , Dilman Alexander D. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation

Abstract: Difluoroboryl complexes obtained from N-acyl hydrazones upon brief treatment with boron trifluoride and allylic silane serve as efficient acceptors of alkyl radicals. The reaction of the boryl chelates with carboxylic acids in the presence of an acridine-type photocatalyst leading to N-acyl hydrazides is described. The efficiency of addition at the C═N bond of the chelates is determined by the formation of a nitrogen-centered radical stabilized by the boron-containing heterocyclic ring.
Cite: Dmitriev I.A. , Levin V.V. , Dilman A.D.
Boron Chelates Derived from N-Acylhydrazones as Radical Acceptors: Photocatalyzed Coupling of Hydrazones with Carboxylic Acids
Organic Letters. 2021. V.23. N22. P.8973-8977. DOI: 10.1021/acs.orglett.1c03501 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000744183900010
Scopus: 2-s2.0-85119444980
OpenAlex: W3212909637
Citing:
DB Citing
OpenAlex 30
Scopus 27
Web of science 30
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