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

[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...

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Bibliographic Details
Published inTetrahedron 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
LanguageEnglish
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
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Summary:[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 generality and excellent stereoselectivity under mild conditions. Experiments indicate that tert-butyl nitrite serves as both NO and NO2 sources and water plays a key role in this difunctionalization reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.10.037