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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 12: 4228 - 4236

DOI: https://doi.org/10.6023/cjoc202006074

Platinum-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides

  • Wang Lin ,
  • Yang Lili ,
  • Ou Yunfu ,
  • Xu Shihai ,
  • Lin Qifu ,
  • Yang Dingqiao
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  • a Analytical and Testing Center, Jinan University, Guangzhou 510632;
    b College of Chemistry and Materials Science, Jinan University, Guangzhou 510632;
    c School of Chemistry, South China Normal University, Guangzhou 510006

Received date: 2020-06-30

  Revised date: 2020-07-23

  Online published: 2020-08-19

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21672084, 21372090) and the Special Fund Project of Department of Natural Resources of Guangdong Province (Guangdong Natural Resources Cooperation) (No. 2020037).

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Abstract

A platinum-catalyzed syn-stereocontrolled ring-opening reaction of oxabicyclic alkenes with arylsulfonyl hydrazides was developed. This protocol exhibited high efficiency and good functional group tolerance, affording cis-2-aryl-1,2-dihydronaphthalen-1-ols (3) or 2-aryl-naphthalenes (4) as dehydrated products in good to excellent yields under mild conditions (up to 89%). In addition, the cis-1,2-configuration of product (1S*,2R*)-6,7-dibromo-2-(p-tolyl)-1,2-dihydronaphthalen-1-ol (3db) was confirmed by X-ray single crystal diffraction analysis. Based on the results, a plausible mechanism for the ring-opening reaction was proposed. Remarkably, arylsulfonyl hydrazides were used as carboanion nucleophiles in the ring-opening reaction via releasing N2 and SO2 in situ.

Key words： platinum catalyst; ring-opening; oxabicyclic alkenes; arylsulfonyl hydrazides; nucleophiles

Cite this article

Wang Lin , Yang Lili , Ou Yunfu , Xu Shihai , Lin Qifu , Yang Dingqiao . Platinum-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides[J]. Chinese Journal of Organic Chemistry, 2020 , 40(12) : 4228 -4236 . DOI: 10.6023/cjoc202006074

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