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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 8: 3144 - 3156

DOI: https://doi.org/10.6023/cjoc202102025

ARTICLES

t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

  • Jiabing Sun ,
  • Tao Miao ,
  • Pinhua Li ,
  • Lei Wang
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  • a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huabei, Anhui 235000
    b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
*Corresponding authors.E-mail: ;
E-mail:

Received date: 2021-02-09

  Revised date: 2021-05-07

  Online published: 2021-05-25

Supported by

National Natural Science Foundation of China(21772062); National Natural Science Foundation of China(22071171); National Natural Science Foundation of China(21602072); Anhui University Natural Science Research Project(KJ2019ZD66)

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Abstract

A t-BuOK-mediated desulfonylation/dehydrogenation cascade reaction of (Z)-C6-(vinyl sulfone)phenanthridines is described. This process provides a novel and efficient strategy for the synthesis of 1,3-dienes with phenanthridinyl units in good yields under transition-metal-free conditions. Furthermore, the application of the generated 1,3-dienes in the [4+2] cycloaddition has been demonstrated by reacting with dienophiles such as fumaronitrile in a two-step procedure.

Key words： t-BuOK; desulfonylation; 1,3-conjugated dienes; cycloaddition reactions

Cite this article

Jiabing Sun , Tao Miao , Pinhua Li , Lei Wang . t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3144 -3156 . DOI: 10.6023/cjoc202102025

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