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. 2021 May 10;60(20):11211-11216.
doi: 10.1002/anie.202101104. Epub 2021 Apr 7.

Stereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions

Xin-Peng Mu  1 , Yuan-He Li  2 , Nan Zheng  1 , Jian-Yu Long  1 , Si-Jia Chen  1 , Bing-Yan Liu  1 , Chun-Bo Zhao  1 , Zhen Yang  1   2   3
Affiliations

Stereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions

Xin-Peng Mu et al. Angew Chem Int Ed Engl. .

Abstract

A novel method for the concise synthesis of cyclohepta[b]indoles in high yields was developed. The method involves a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones. Experimental and computational studies suggested that the reaction is a photoredox process initiated by single-electron oxidation of an enaminone moiety, which undergoes subsequent cyclobutane formation and rapidly fragmentation in a radical-cation state to form cyclohepta[b]indoles.

Keywords: [2+2]/retro-Mannich-type cycloaddition; amine radical cation; cyclohepta[b]indole; photoredox catalysis.

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