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Zn-mediated fragmentation of N-alkoxyphthalimides enabling synthesis of gem-difluoroalkenes
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  • Yiyue Wang,
  • Weijun Pang,
  • Tie Liu,
  • Jing Sun,
  • Mingdong Zhou
Yiyue Wang
Liaoning University of Petroleum and Chemical Technology
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Weijun Pang
Shenyang University of Chemical Technology
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Tie Liu
Liaoning University of Petroleum and Chemical Technology
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Jing Sun
Liaoning University of Petroleum and Chemical Technology
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Mingdong Zhou
Shenyang University of Chemical Technology

Corresponding Author:mingdong.zhou@hotmail.com

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Abstract

Alkoxy radicals have emerged as versatile intermediates to synthesis various organic molecules, and the development of convenient methods for their generation is highly desired. In this work, a new method for the facile access to alkoxy radicals from bench-stable N-alkoxyphthalimides promoted by Zn has been developed for the first time. These alkoxyl radicals subsequently undergo β-scission or hydrogen atom transfer to produce diverse and valuable alkyl radical species, which can be further trapped by α-trifluoromethyl alkenes to construct structurally diverse gem-difluoroalkenes in good yields.