141091-37-4Relevant articles and documents
Copper(i)-catalysed regio- and diastereoselective intramolecular alkylboration of terminal allenes: via allylcopper(i) isomerization
Ozawa, Yu,Iwamoto, Hiroaki,Ito, Hajime
, p. 4991 - 4994 (2018)
We report the first copper(i)-catalysed intramolecular alkylboration of terminal allenes with an alkyl halide moiety. The reaction provides alkenylboronates bearing a four-membered ring structure with high regio- and diastereocontrol. A possible reaction mechanism is proposed, involving the facile isomerization of an allylcopper(i) intermediate. A DFT study explains the experimental regio- and diastereoselectivity.
Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization
Selander, Nicklas,Willy, Benjamin,Szabo, Kaiman J.
, p. 4051 - 4053 (2010)
(Figure Presented) The C-H borylation of simple alkenes catalyzed by palladium pincer complex 1 was performed in the presence of hypervalent iodine and bis(pinacolato)diboron compounds. The borylation reaction probably occurs by a PdIIPdIVoxidationdiboronate transmetalation sequence. TFA = trifluoroacetate.
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.
Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
, p. 18118 - 18127 (2020/11/26)
The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
