Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates

被引：25
作者：
Li, Yue [1 ]
Yang, Wen [1 ]
Cheng, Guo [1 ]
Yang, Dingqiao [1 ]
机构：
[1] S China Normal Univ, Sch Chem & Environm, Key Lab Theoret Chem Environm, Minist Educ, Guangzhou 510006, Guangdong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 11期
基金：
中国国家自然科学基金;
关键词：
CROSS-COUPLING REACTION; AZABICYCLIC ALKENES; BICYCLIC OLEFINS; 2-SUBSTITUTED 1,2-DIHYDRO-1-NAPHTHOLS; DIRECT SULFONYLATION; ARYLBORONIC ACIDS; BORONIC ACIDS; OXABENZONORBORNADIENES; ARYL; ARYLATION;
D O I：
10.1021/acs.joc.6b00667
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed syn-stereocontrolled ring opening reactions of oxabenzonorbornadienes with a wide range of sodium arylsulfinates were investigated, affording the desired products in good to excellent yields under an air atmosphere. This protocol provides a low-cost new viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ol with good functional group tolerance. In addition, the cis configuration of 3da was established by X-ray diffraction analysis, and a plausible mechanism, for the ring opening reaction was proposed.
引用
收藏
页码：4744 / 4750
页数：7
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