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Synthesis 2019; 51(02): 522-529
DOI: 10.1055/s-0037-1610907
paper
© Georg Thieme Verlag Stuttgart · New York

Visible-Light Photoredox-Catalyzed Cascade Reaction for the Synthesis of Pyrrolo[2,1-a]isoquinoline-Substituted Phosphonates

Lingna Wang
,
Tiancong Ma
,
Mingming Qiao
,
Qiangxian Wu
,
Deqing Shi*
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China   Email: chshidq@mail.ccnu.edu.cn
,
Wenjing Xiao
› Author AffiliationsWe are grateful to the NSFC (No. 21342004 and 51573066), Program of Introducing Talents of Discipline to Universities of China (111 Program, B17019) and the Syngenta Ph.D. (postgraduate) program for support of this research.
Further Information

Publication History

Received: 06 August 2018

Accepted after revision: 21 August 2018

Publication Date:
17 September 2018 (online)

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Abstract

A visible-light photoredox-catalyzed oxidation/[3+2] cycloaddition/oxidative aromatization cascade reaction of [(3,4-dihydroisoquinolin-2(1H)-yl)methyl]phosphonates and activated olefins or alkynes for the efficient synthesis of potentially biological active pyrrolo[2,1-a]isoquinoline-substituted phosphonates was developed. This transformation features mild reaction conditions (i.e., visible light irradiation, room temperature), molecular oxygen (O2) as a green oxidant, simple ‘one-pot’ operation.

Key words

visible light catalysis - [3+2] cycloaddition - pyrrolo[2,1-a]isoquinoline - phosphonate - cascade reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610907.
  • Supporting Information
 

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