Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4228-4236.DOI: 10.6023/cjoc202006074 Previous Articles     Next Articles


王林a,c, 杨丽丽a, 欧云付a, 徐石海a,b, 林啟福c, 杨定乔c   

  1. a 暨南大学分析测试中心 广州 510632;
    b 暨南大学化学与材料学院 广州 510632;
    c 华南师范大学化学学院 广州 510006
  • 收稿日期:2020-06-30 修回日期:2020-07-23 发布日期:2020-08-19
  • 通讯作者: 徐石海, 杨定乔;
  • 基金资助:

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

Wang Lina,c, Yang Lilia, Ou Yunfua, Xu Shihaia,b, Lin Qifuc, Yang Dingqiaoc   

  1. 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:2020-06-30 Revised:2020-07-23 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).

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