Synthesis of α,β-Unsaturated N-Aryl Ketonitrones from Oximes and Diaryliodonium Salts: Observation of a Metal-Free N-Arylation Process

Xiao Pan Ma, Wei Min Shi, Xue Ling Mo, Xiao Hua Li, Liang Gui Li, Cheng Xue Pan, Bo Chen, Gui Fa Su, Dong Liang Mo

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37 Scopus citations

Abstract

An efficient transition-metal-free method for the preparation of α,β-unsaturated N-aryl ketonitrones under mild conditions has been developed. This reaction shows good functional group tolerance for both electron-rich and electron-deficient substituents on both oximes and diaryliodonium salts. Two examples of gram-scale preparations have been realized in good yields. Further transformations of these nitrones to different N-heterocycles have been demonstrated. DFT calculations suggest that N-arylation products are formed by [1,3]-phenyl migration of an O-coordinated oximate complex via a four-centered transition state, while the O-arylation products are formed by [1,3]-phenyl migration of a N-coordinated oximate complex.

Original languageEnglish (US)
Pages (from-to)10098-10107
Number of pages10
JournalJournal of Organic Chemistry
Volume80
Issue number20
DOIs
StatePublished - Oct 16 2015

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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