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Metal‐Free C(sp 3 )‐O Bond Formation through Radical Translocation: A Mild, Efficient, and Practical Approach to α‐Alkoxybenzamides
Author(s) -
Huang FengQing,
Zhou GuoXiu,
Dong Xin,
Qi LianWen,
Zhang Bo
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500495
Subject(s) - chemistry , iminium , ascorbic acid , reagent , radical ion , nucleophile , radical , nitrite , metal , photochemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , ion , food science , nitrate
A mild and metal‐free method to functionalize aliphatic C−H bonds adjacent to a nitrogen atom through radical translocation, oxidation to an iminium intermediate, and nucleophilic trapping with alcohols is described. The transformation proceeds efficiently with edible ascorbic acid (vitamin C) as the radical initiator and readily available tert ‐butyl nitrite as the nitrosating reagent. Notably, any transition‐metal or additive is not required. The current method provides simple, efficient, and practical access to valuable α‐alkoxybenzamides in moderate to good yields.