Oxidative radical addition–chlorination of alkenes to access 1, 1-dichloroalkanes from simple reagents. Issue 12 (7th May 2019)

• Record Type: Journal Article
• Authors: Chen, Cui; Li, Yibiao; Pan, Yupeng; Duan, Linhai; Liu, Weibing
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 12(2019)
• Page Start: 2032
• Page End: 2036
• Publication Date: 2019-05-07
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo00400a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : This protocol provides a facile regioselective method for the synthesis of 1, 1-dichloroalkanes from terminal alkenes using simple chloro reagents. Abstract : The oxidative radical addition of alkenes has been achieved using a simple chlorine source in the presence of tert -butyl hydroperoxide under mild conditions. A series of anti-Markovnikov aryl chlorides were obtained in good to excellent yields with a broad substrate scope. Notably, the dichloroaryl compounds were successfully obtained under metal-free conditions, providing an easy method for the direct preparation of 1, 1-dichloroalkanes. Furthermore, these reactions were performed in an open flask without inert gas protection, which is favorable for the future scale-up of this synthetic process. The mechanistic study suggested the involvement of a radical pathway.