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

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

研究论文

铂催化氧杂二环烯烃与芳基磺酰肼的顺式-立体控制开环反应

  • 王林 ,
  • 杨丽丽 ,
  • 欧云付 ,
  • 徐石海 ,
  • 林啟福 ,
  • 杨定乔
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  • 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

  网络出版日期: 2020-08-19

基金资助

国家自然科学基金（Nos.21672084，21372090）和广东省自然资源厅专项资金（粤自然资合）（No.2020037）资助项目.

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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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摘要

开发了一种铂催化氧杂二环烯烃与芳基磺酰肼的顺式-立体控制开环反应.该方法显示出高效性和良好的官能团耐受性，在温和条件下能以高达89%的产率得到顺式-2-芳基-1，2-二氢萘-1-醇（3）或脱水产物2-芳基萘（4）.此外，通过X射线单晶衍射分析确认了产物（1S*，2R*）-6，7-二溴-2-（4-甲基苯基）-1，2-二氢萘-1-醇（3db）的顺式-1，2-构型.根据实验结果，提出了一种合理的开环反应机理.值得注意的是，在开环反应中，芳基磺酰肼通过释放N2和SO2形成碳负离子作为亲核试剂.

关键词： 铂催化剂; 开环; 氧杂二环烯烃; 芳基磺酰肼; 亲核试剂

本文引用格式

王林 , 杨丽丽 , 欧云付 , 徐石海 , 林啟福 , 杨定乔 . 铂催化氧杂二环烯烃与芳基磺酰肼的顺式-立体控制开环反应[J]. 有机化学, 2020 , 40(12) : 4228 -4236 . DOI: 10.6023/cjoc202006074

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

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