Catalytic Aerobic Sulfonyloximation of Alkenes Enabled by the Nitric Oxide-Donor Role of 2-Nitropropane

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초록

Aerobic sulfonyloximation of alkenes has been developed using the commodity chemical 2-nitropropane as dual sources of α-nitroalkyl radicals and nitric oxide (NO) under cooperative KSeCN/TBAI phase transfer catalysis. This method enables concurrent C–SO2R and C–NO bond formation through a radical redox relay involving aerobic nitro–nitrite isomerization and NO fragmentation. Structurally diverse β-sulfonyl oximes with broad substrate scope are obtained under mild conditions, highlighting the potential of controlled NO incorporation in radical transformations.

키워드

NEF REACTIONNITROALKANESSULFONYLATIONDEAMINATIONEFFICIENTCHEMISTRYOXIMATIONMECHANISMOXYGEN
제목
Catalytic Aerobic Sulfonyloximation of Alkenes Enabled by the Nitric Oxide-Donor Role of 2-Nitropropane
저자
Thorve, Pradip RamdasJo, HyeonminKim, Hun YoungOh, Kyungsoo
DOI
10.1021/acs.orglett.6c01681
발행일
2026-05
유형
Article; Early Access
저널명
Organic Letters
28
23
페이지
7224 ~ 7229