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苄基硫醚形成与铜催化相结合。

Benzyl thioether formation merging copper catalysis.

作者信息

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

机构信息

School of Pharmacy, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China

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.

出版信息

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

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) 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 S1-type nucleophilic attack of the carbocations formed .

摘要

已开发出一种新型铜催化的硫醚化反应,以中等至优异的产率得到苄基硫醚。在温和且易于操作的条件下,在作为路易斯酸催化剂的Cu(OTf)存在下,由容易获得的苄醇(伯、仲和叔醇)和硫醇高效制备各种硫醚。这种C-S键形成方案具有出色的化学选择性,初步机理研究表明该反应应通过路易斯酸介导的对所形成碳正离子的S1型亲核进攻进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e8c/8697992/6ec74dff49ce/d1ra08015f-s1.jpg

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