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Metal-Free Photocatalytic Generation and Alkynylation of Carbamoyl Radicals: a Facile Synthesis of Alkynyl Amides
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  • Yu Zhao,
  • Qiuyu Zhang,
  • kai Zhang,
  • yubin Bai,
  • Jinfeng Li,
  • xiaojun Yang,
  • yurong Duan,
  • tongtong Xing
Yu Zhao
Yan'an University

Corresponding Author:zhaoyyau@163.com

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Qiuyu Zhang
Northwestern Polytechnical University
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kai Zhang
Jiangsu Normal University
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yubin Bai
Yan'an University
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Jinfeng Li
Yan'an University
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xiaojun Yang
Yan'an University
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yurong Duan
Yan'an University
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tongtong Xing
Yan'an University
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Abstract

A metal-free photocatalytic alkynylation of carbamoyl radical for facile synthesis of alkynyl amides was described. This reaction utilized 4-carbamoyl 1,4-dihydropyridines as carbamoyl radical precursors, under visible light irradiation, reacted with hypervalent iodine(III) reagents through radical addition process. This protocol features well functional group tolerance, and broad substrate scope, for direct synthesis of alkynyl amide derivatives in good to excellent yields under mild and redox-neutral reaction conditions. The synthetic application is further demonstrated by the late-stage installation of alkynyl amides into the natural product and active pharmaceutical relevant molecules. The mechanistic studies indicated that simultaneous existance between photoredox catalytic and direct photoexcited processes.