Oxidative radical addition-chlorination of alkenes to access 1,1-dichloroalkanes from simple reagents

Chen, Cui1; Li, Yibiao2; Pan, Yupeng3; Duan, Linhai1; Liu, Weibing1

2019-06-21

10.1039/c9qo00400a

Organic Chemistry Frontiers   影响因子和分区

2052-4129

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.

SCI ; EI ; IC ; CCR

英语

其他

Chemistry

Chemistry, Organic

WOS:000473641300015

ROYAL SOC CHEMISTRY

20192407053747

Chlorine compounds ; Inert gases

Organic Compounds:804.1 ; Inorganic Compounds:804.2

Web of Science

1.Guangdong Univ Petrochem Technol, Coll Chem Engn, 2 Guandu Rd, Maoming 525000, Peoples R China
2.Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529090, Guangdong, Peoples R China
3.Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China

Chen, Cui,Li, Yibiao,Pan, Yupeng,et al. Oxidative radical addition-chlorination of alkenes to access 1,1-dichloroalkanes from simple reagents[J]. Organic Chemistry Frontiers,2019,6(12):2032-2036.

Chen, Cui,Li, Yibiao,Pan, Yupeng,Duan, Linhai,&Liu, Weibing.(2019).Oxidative radical addition-chlorination of alkenes to access 1,1-dichloroalkanes from simple reagents.Organic Chemistry Frontiers,6(12),2032-2036.

Chen, Cui,et al."Oxidative radical addition-chlorination of alkenes to access 1,1-dichloroalkanes from simple reagents".Organic Chemistry Frontiers 6.12(2019):2032-2036.