title: TBAF-mediated reactions of 1,1-dibromo-1-alkenes with thiols and amines and regioselective synthesis of 1,2-heterodisubstituted alkenes.
abstract: An efficient synthesis of trisubstituted alkenes including 1,2-heterodisubstituted alkenes has been described. Reactions of thiols and amines with 1,1-dibromo-1-alkenes in the presence of TBAF·3H(2)O afford (Z)-2-bromovinyl sulfides and (Z)-2-bromovinyl amines regio- and stereoselectively. The reaction proceeds under catalyst-free conditions with high efficiency. The coupling reactions of the obtained products bearing bromine atoms with phenylacetylene and phenylboronic acid gave trisubstituted alkenes in good to excellent yields. Cross-coupling with various N, O, S, and P nucleophiles selectively generated 1,2-N,O, 1,2-N,S, 1,2-S,P, 1,2-S,S, and 1,2-S,O heterodisubstituted alkenes.
authors.affiliation: Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, People's Republic of China.
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
authors.forename: Shaojin
authors.initials: S
authors.lastname: Gu
authors.forename: Wanzhi
authors.initials: W
authors.lastname: Chen
authors.forename: Dacheng
authors.initials: D
authors.lastname: Li
authors.forename: Jianmin
authors.initials: J
authors.lastname: Dou
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis; D001966:Bromine / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000475:Alkenes; D000588:Amines; D001897:Boronic Acids; D000644:Quaternary Ammonium Compounds; D013438:Sulfhydryl Compounds; D014753:Vinyl Compounds; C044736:phenylacetylene; C009405:tetrabutylammonium; C010686:benzeneboronic acid; D000114:Acetylene; D001966:Bromine