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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 12: 4282 - 4291

DOI: https://doi.org/10.6023/cjoc202211011

ARTICLES

Visible-Light-Driven Photocatalytic Kharasch Reaction of Phenol/ Arylamine-Linked 1,6-Enynes with Perhalogenated Methane

  • Xiaoshuang Ji ,
  • Rong Fu ,
  • Shuliang Wang ,
  • Wenjuan Hao ,
  • Bo Jiang
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  • School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
*E-mail: ;

Received date: 2022-11-08

  Revised date: 2022-11-22

  Online published: 2022-11-28

Supported by

National Natural Science Foundation of China(21971090)

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Abstract

Radical annulative carbohalofunctionalization of 1,n-enynes via atom transfer processes constitutes an efficient and practical synthetical strategy for accessing halogenated cyclic structures with complete atom economy through radical cleavage of a pre-existing carbon-halogen σ-bond of an atom transfer reagent and their transposition over the π-bond of enyne motifs. Recently, such reaction has become one of hot topics. A general photocatalytic annulative carbohalogenation of phenol/arylamine-linked 1,6-enynes with perhalogenated methanes such as BrCCl3 or CBr4 is disclosed, leading to the atom-economic, efficient synthesis of functionalized (Z)-2,3-dihydrobenzofurans and (Z)-indolines as main stereoisomers with good yields and high stereoselectivity under mild and oxidant-free conditions, in which only (Z)-configuration was observed in most products. This protocol demonstrates wide substrate scope, high functional group tolerance, and high atom economy as well as high stereoselectivity, providing a green, atom-economic and efficient method toward 2,3-dihydrobenzofurans and indolines.

Key words： photocatalysis; annulative carbohalogenation; atom economy; 2,3-dihydrobenzofurans

Cite this article

Xiaoshuang Ji , Rong Fu , Shuliang Wang , Wenjuan Hao , Bo Jiang . Visible-Light-Driven Photocatalytic Kharasch Reaction of Phenol/ Arylamine-Linked 1,6-Enynes with Perhalogenated Methane[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4282 -4291 . DOI: 10.6023/cjoc202211011

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