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.
Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui
supporting information, p. 5815 - 5821 (2020/09/21)
We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.