Benzyl thioether formation merging copper catalysis

Bing Xu; Ying Lin; Yang Ye; Li Xu; Tian Xie; Xiang-Yang Ye

doi:10.1039/d1ra08015f

Benzyl thioether formation merging copper catalysis

RSC Adv. 2021 Dec 23;12(2):692-697. doi: 10.1039/d1ra08015f. eCollection 2021 Dec 22.

Authors

Bing Xu^{1

2}, Ying Lin^{1

2}, Yang Ye^{1

2}, Li Xu^{1

2}, Tian Xie^{1

2}, Xiang-Yang Ye^{1

2}

Affiliations

¹ School of Pharmacy, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China yangye@hznu.edu.cn.
² Key Laboratory of Elemene Class Anti-Cancer Chinese Medicines, Engineering Laboratory of Development and Application of Traditional Chinese Medicines, Collaborative Innovation Center of Traditional Chinese Medicines of Zhejiang Province, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China.

Abstract

A novel copper-catalyzed thioetherification reaction has been developed to afford benzyl thioethers in moderate to excellent yields. Under the mild and easy-to-operate conditions, a variety of thioethers are efficiently prepared from readily available benzyl alcohols (primary, secondary, and tertiary) and thiols in the presence of Cu(OTf)₂ as the Lewis acid catalysis. This C-S bond formation protocol furnishes exceptional chemoselectivity, and the preliminary mechanism studies show that the reaction should proceed through a Lewis-acid-mediated S_N1-type nucleophilic attack of the carbocations formed in situ.