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

doi:10.6023/cjoc202006074

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

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

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 E-mail:txush@jnu.edu.cn;yangdq@scnu.edu.cn
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.

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

Wang Lin^a,c, Yang Lili^a, Ou Yunfu^a, Xu Shihai^a,b, Lin Qifu^c, Yang Dingqiao^c

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).

1. cjoc202006074辅助材料.pdf(3792KB)

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.

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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

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

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