Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 20, Pages 10098-10107Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01716
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Funding
- Guangxi Normal University [2014ZD005]
- National Natural Science Foundation of China [21462008]
- Ministry of Education of China [IRT1225]
- U.S. Department of Energy [DESC0001057]
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An efficient transition-metal-free method for the preparation of alpha,beta-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.
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