862126-34-9Relevant academic research and scientific papers
Cobalt(I)-mediated preparation of polyborylated cyclohexadienes: Scope, limitations, and mechanistic insight
Geny, Anais,Lebaeuf, David,Rouquie, Gabriel,Vollhardt, K. Peter C.,Malacria, Max,Gandon, Vincent,Aubert, Corinne
, p. 5408 - 5425 (2007)
A series of 1,3- and 1,4-di-boryl-1,3-cyclohexadiencs have been prepared by intermolecular CoCp-mediated [2+2+2] cocyclizations of alkynylboronic pinacolate esters with alkenes, followed by oxidative demetallation with iron(III) chloride. The effect of su
Aluminium-Catalyzed C(sp)?H Borylation of Alkynes
Willcox, Dominic R.,De Rosa, Daniel M.,Howley, Jack,Levy, Abigail,Steven, Alan,Nichol, Gary S.,Morrison, Carole A.,Cowley, Michael J.,Thomas, Stephen P.
supporting information, p. 20672 - 20677 (2021/08/20)
Historically used in stoichiometric hydroalumination chemistry, recent advances have transformed aluminium hydrides into versatile catalysts for the hydroboration of unsaturated multiple bonds. This catalytic ability is founded on the defining reactivity of aluminium hydrides with alkynes and alkenes: 1,2-hydroalumination of the unsaturated π-system. This manuscript reports the aluminium hydride catalyzed dehydroborylation of terminal alkynes. A tethered intramolecular amine ligand controls reactivity at the aluminium hydride centre, switching off hydroalumination and instead enabling selective reactions at the alkyne C?H σ-bond. Chemoselective C?H borylation was observed across a series of aryl- and alkyl-substituted alkynes (21 examples). On the basis of kinetic and density functional theory studies, a mechanism in which C?H borylation proceeds by σ-bond metathesis between pinacolborane (HBpin) and alkynyl aluminium intermediates is proposed.
