35802-48-3Relevant articles and documents
Regioselective Access to α-Vinylsilanes and α-Vinylgermanes by Cobalt-Catalyzed Migratory Hydrofunctionalization of 2-Alkynes
Chang, Sukbok,Kim, Dongwook,Park, Jung-Woo,Sahoo, Manoj Kumar
, p. 12777 - 12784 (2021/10/29)
While migratory functionalization of alkynes has been recognized as a unique way to access allylic functionalities via π-allyl metal intermediates, hydrofunctionalization of 2-alkynes to afford α-functional olefins has been unexplored. We describe herein the use of a cobalt hydride based system for regioselective migratory hydrofunctionalization of 2-alkynes to furnish α-vinylsilanes and α-vinylgermanes by a mechanistic understanding of the cobalt hydride species on alkyne π-bond migration. The key mechanism of alkyne π-bond migration by [bis(dicyclohexylphosphino)ethane]cobalt hydride is strongly supported by both experimental and computational studies, and the role of each reaction component, such as alkynes and silanes, is elucidated to rationalize the unique α-vinyl selectivity.
Free radical addition to branched allylsilanes: Stereoselective formation and elimination of β bromosilanes
Porter, Ned A.,Zhang, Guiru,Reed, Aimee D.
, p. 5773 - 5777 (2007/10/03)
Lewis acid-promoted free radical addition to 3-silyl-1-butenes occurs in good yield to give predominantly the cis-substituted alkene. The transfer reaction occurs by atom-transfer addition of the alkyl bromide precursor, an addition that occurs by Felkin-
ORGANIC SYNTHESIS WITH REAGENTS DERIVED FROM 3R3SiMgMe AND MnCl2
Fugami, Keigo,Hibino, Jun-ichi,Nakatsukasa, Shigeki,Matsubara, Seijiro,Oshima, Koichiro,et al.
, p. 4277 - 4292 (2007/10/02)
Synthetically useful reactions mediated by reagents derived from 3 equiv. of R3SiMgMe and MnCl2 are disclosed. (1) The manganese species reacted with terminal acetylenes to give 1,2-disilylated 1-alkenes.Mono- and bis(trimethylsilyl)acetylenes gave tri- a