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Transition-Metal-Free β-C-H Bond Carbonylation of Enamides or Amides with a Trifluoromethyl Group as CO Surrogate for the Synthesis of 1,3-Oxazin-6-ones

Ping Song, Peng Yu, Jin-Shun Lin, Yiqun Li*, Ning-Yuan Yang and Xin-Yuan Liu*

*Department of Chemistry, Jinan University, Guangzhou, Guangdong 510632; Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China, Japan, Email: tlyqjnu.edu.cn, liuxy3sustc.edu.cn

P. Song, P. Yu, J.-S. Lin, Y. Li, N.-Y. Yang, X.-Y. Liu, Org. Lett., 2017, 19, 1330-1333.

DOI: 10.1021/acs.orglett.7b00178 (free Supporting Information)


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Abstract

In a cascade β-C-H bond trifluoromethylation/C(sp3)-F bond activation/hydrolysis reaction of enamides with Togni's reagent, the CF3 group acts as a CO surrogate to provide 1,3-oxazin-6-ones in good yields, including synthetically or pharmaceutically important compounds, which are difficult to access by known methods.

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Key Words

N-heterocycles, O-heterocycles


ID: J54-Y2017