Copper-Catalyzed Diastereoselective 1,2-Difunctionalization of Oxabenzonorbornadienes Leading to β-Thiocyanato Thioethers

Qifu Lin; Wen Yang; Yongqi Yao; Shuqi Chen; Yun Tan; Donghan Chen; Dingqiao Yang

doi:10.1021/acs.orglett.9b02452

Copper-Catalyzed Diastereoselective 1,2-Difunctionalization of Oxabenzonorbornadienes Leading to β-Thiocyanato Thioethers

Org Lett. 2019 Sep 20;21(18):7244-7247. doi: 10.1021/acs.orglett.9b02452. Epub 2019 Aug 27.

Authors

Qifu Lin^{1

2}, Wen Yang¹, Yongqi Yao¹, Shuqi Chen¹, Yun Tan¹, Donghan Chen¹, Dingqiao Yang¹

Affiliations

¹ Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, College of Chemistry , South China Normal University , Guangzhou 510006 , People's Republic of China.
² College of Marine Sciences , Beibu Gulf University , Qinzhou 535011 , People's Republic of China.

PMID: 31453705
DOI: 10.1021/acs.orglett.9b02452

Abstract

A novel copper-catalyzed complete diastereoselective 1,2-difunctionalization of oxabicyclic alkenes has been developed. Two C-S bonds were constructed simultaneously on the oxabenzonorbornadienes leading to β-thiocyanato thioethers through the three-component (oxabicyclic alkenes, aryl iodides, and potassium thiocyanate), one-pot reaction. Various functional groups attached to the substrates were tolerated in this protocol to afford the corresponding β-thiocyanato thioether products in moderate yields.