title: An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes.
abstract: An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents.
authors: Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China.
authors: Zhaozhen
authors: Z
authors: Yang
authors: Xiaoyi
authors: X
authors: Chen
authors: Wei
authors: W
authors: Kong
authors: Siyuan
authors: S
authors: Xia
authors: Renwei
authors: R
authors: Zheng
authors: Fang
authors: F
authors: Luo
authors: Gangguo
authors: G
authors: Zhu
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D000480:Alkynes; D006846:Hydrocarbons, Halogenated; D013438:Sulfhydryl Compounds; D013440:Sulfides