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Synlett 2023; 34(02): 143-148
DOI: 10.1055/a-1946-7691
letter

Photocatalytic Decarboxylative Cyclization of 1,6-Enynes and N-Methacryloyl-2-phenylbenzimidazoles by Potassium Iodide/ Triphenylphosphine Catalysis

Jian Zhang
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, P. R. of China
,
Jiao-Zhe Li
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, P. R. of China
,
Ling-Tao Wang
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, P. R. of China
,
Xuan-Chi Yu
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, P. R. of China
,
Jun-Hao Zhang
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, P. R. of China
,
Guo-Ping Ge∗
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, P. R. of China
,
Hongxin Liu∗
b   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 325035, P. R. of China
,
Wen-Ting Wei∗
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, P. R. of China
› Author AffiliationsWe thank the Fundamental Research Funds for the Provincial Universities of Zhejiang (SJLY2021004), and Education Foundation of ­Zhejiang Province (Y202146200) for financial support.
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Abstract

We describe a photocatalytic decarboxylative cyclization of 1,6-enynes or N-methacryloyl-2-phenylbenzimidazoles for efficient and ecofriendly syntheses of lactams or benzimidazo[2,1-a]isoquinoline-6(5H)-ones, respectively, by the use of KI/PPh3 as a redox catalyst system. In this method, N-hydroxyphthalimide esters were used as alkyl-radical precursors to achieve this decarboxylative cyclization without any dyes, transition-metal catalysts, oxidants, or bases.

Keywords

green chemistry - photocatalysis - transition-metal free - cyclization - lactams - benzimidazoquinolinones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1946-7691.
  • Supporting Information


Publication History

Received: 04 August 2022

Accepted after revision: 19 September 2022

Accepted Manuscript online:
19 September 2022

Article published online:
21 November 2022

© 2022. Thieme. All rights reserved

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