title: Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents.
abstract: A copper-free allylic arylation reaction between 3,3-disubstituted allylic halides and triazene-softened aryl Grignard reagents has been developed. This protocol presents a direct and efficient way to construct both α- or γ-isomers with high regioselectivity under environmentally benign conditions. Various functional groups can be tolerated in the reaction and the products are of high value for multiple synthetic applications. The α- and γ-isomers can be converted to the corresponding 3H-indole and indole derivatives in multigram scale respectively.
authors.affiliation: Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China. renhj@zstu.edu.cn.
authors.forename: Lijun
authors.initials: L
authors.lastname: Xu
authors.forename: Zhubo
authors.initials: Z
authors.lastname: Liu
authors.forename: Weipeng
authors.initials: W
authors.lastname: Dong
authors.forename: Jinyu
authors.initials: J
authors.lastname: Song
authors.forename: Maozhong
authors.initials: M
authors.lastname: Miao
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Xu
authors.forename: Hongjun
authors.initials: H
authors.lastname: Ren
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014226:Triazenes / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D007211:Indoles; D009942:Organometallic Compounds; D014226:Triazenes; C050431:allyl bromide; C023698:allyl chloride