gem-Silylborylation approach for tri- and tetrametalmethanes: the first synthesis of boryl(germyl)(silyl)(stannyl)methanes

• Published in: Journal of organometallic chemistry Vol. 686; no. 1; pp. 286 - 293
• Main Authors: Shimizu, Masaki, Kurahashi, Takuya, Kitagawa, Hirotaka, Shimono, Katsuhiro, Hiyama, Tamejiro
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.11.2003; Elsevier
• Subjects: Boron; Carbenoid; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; gem-Silylborylation; Halomethane; Physical Sciences; Science & Technology; Silicon; Silylborane; Tetrametalmethane; Boron; Tetrametalmethane; Silylborane; gem-Silylborylation; Silicon; Halomethane; Carbenoid; halomethane; REAGENTS; CARBENOIDS; gem -silylborylation; FC(SIME3); REACTIVITY; silylborane; BORONIC ESTERS; silicon; OLEFINATION; tetrametalmethane; CHEMISTRY; GENERATION; STEREOSELECTIVE-SYNTHESIS; boron; HOMOLOGATION; carbenoid
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/S0022-328X(03)00561-8

gem-Silylborylation of halomethyllithiums with silylboranes allows us to prepare boryl(silyl)methanes substituted by such heteroatoms as Cl, Br, I, O, S, Si, Ge, and Sn in high yields. With B, Si, and Sn- or B, Ge, and Si-substituted methanes, the first synthesis of B, Ge, Si, and Sn-substituted methanes was achieved via deprotonation of the trimetalated methane followed by germylation with Me 3GeCl or stannylation with Bu 3SnCl, respectively. Novel synthesis of functionalized boryl(silyl)methanes via gem-silylborylation of halomethyllithiums is described. Furthermore, the first synthesis and X-ray analysis of boron-, germane-, silicon-, and tin-substituted methanes are also reported.