HFIP-Assisted Denitrogenative Radical Fragmentation Pathway of Areneazo-2-(2-nitro)propanes: Cross-Coupling of Aryl Radicals with Alkynes and Coupling Reagents
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초록

The HFIP-assisted denitrogenative radical fragmentation of areneazo-2-(2-nitro)propanes, a safer alternative to diazonium salts, generated dinitrogen, nitrogen monoxide, acetone, and aryl radicals. These in situ generated aryl radicals participated in [4 + 2] benzannulations to form phenanthrenes and in diverse cross-coupling reactions, including Sandmeyer-type C-Br/C-Bpin/C-S/C-Se/C-P and C-C bond formations. TEMPO-trapping experiments confirmed their transient nature, enabling versatile approaches to radical-mediated C-C and C-X bond construction under mild and practical conditions.

키워드

AcetoneGlyceryl TrinitrateHexafluoro 2 PropanolNitric OxideNitrous OxidePropaneAcetoneAlkyneDiazonium CompoundGlyceryl TrinitrateHexafluoro 2 PropanolNitric OxideNitrous OxidePhenanthrene DerivativePropaneReagentArticleControlled StudyCross Coupling ReactionDrug AnalysisDrug DevelopmentNonhuman4+2 BENZANNULATIONDIRECT CONVERSIONASCORBIC-ACIDARYLATIONARYLAMINESANILINESQUINOXALIN-2(1H)-ONESDEAMINATIONMECHANISMSGENERATION
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HFIP-Assisted Denitrogenative Radical Fragmentation Pathway of Areneazo-2-(2-nitro)propanes: Cross-Coupling of Aryl Radicals with Alkynes and Coupling Reagents
저자
Kim, DaeunKim, Hun YoungOh, Kyungsoo
DOI
10.1021/acs.orglett.5c02494
발행일
2025-08
유형
Article; Early Access
저널명
Organic Letters
27
31
페이지
8563 ~ 8567