Water-controlled nitro-oximation of alkenes under catalyst-free conditions

• Published in: Tetrahedron letters Vol. 59; no. 48; pp. 4272 - 4275
• Main Authors: Tang, Lin, Yang, Zhen, Chang, Xueping, Zou, Guodong, Zhou, Yuqiang, Rao, Weihao, Ma, Xiantao, Zhao, Geng
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.11.2018; Elsevier
• Subjects: Alkenes; C[sbnd]N bond formation; Catalyst-free; Chemistry; Chemistry, Organic; Difunctionalization; Physical Sciences; Science & Technology; Water; Water; Difunctionalization; Alkenes; Catalyst-free; CN bond formation; SODIUM TRIFLUOROMETHANESULFINATE; C-N bond formation; C-N; AEROBIC OXYSULFONYLATION; HIGHLY EFFICIENT; 3-COMPONENT OXYTRIFLUOROMETHYLATION; SULFINIC ACIDS; VICINAL DIFUNCTIONALIZATION; SELECTIVE SYNTHESIS; TERT-BUTYL NITRITE; METAL-FREE

[Display omitted] •No use of any catalyst.•No external oxidant and additive.•Reaction in aqueous media.•Gram-scale synthesis. A convenient and precise nitration and oximation of alkenes with tert-butyl nitrite has been reported, yielding α-nitro ketoximes in satisfactory yields with broad substrate...