title: Stereoselective cross-coupling reaction of 1,1-Diboryl-1-alkenes with electrophiles: a highly stereocontrolled approach to 1,1,2-triaryl-1-alkenes.
abstract: Palladium-catalyzed cross-coupling reaction of 1,1-diboryl-1-alkenes with aryl and alkenyl iodides was found to proceed stereoselectively, giving rise to the corresponding mono-coupled product as a single diastereomer with E-configuration. Second coupling of the initial product with another aryl iodide affords diverse triarylalkenes in their stereochemically pure form. This highly stereoselective approach for triarylalkenes allows one to synthesize both diastereomers in one pot from 1,1-diboryl-1-alkenes.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. shimizu@npc05.kuic.kyoto-u.ac.jp
authors.forename: Masaki
authors.initials: M
authors.lastname: Shimizu
authors.forename: Chihiro
authors.initials: C
authors.lastname: Nakamaki
authors.forename: Katsuhiro
authors.initials: K
authors.lastname: Shimono
authors.forename: Michael
authors.initials: M
authors.lastname: Schelper
authors.forename: Takuya
authors.initials: T
authors.lastname: Kurahashi
authors.forename: Tamejiro
authors.initials: T
authors.lastname: Hiyama
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001896:Boron Compounds; D003432:Cross-Linking Reagents