84736-47-0Relevant articles and documents
Use of polymer-supported dialkylphosphinobiphenyl ligands for palladium-catalyzed amination and Suzuki reactions
Parrish,Buchwald
, p. 3820 - 3827 (2001)
The preparations of polymer-supported dialkylphosphinobiphenyl ligands (3) are reported. A palladium catalyst based on ligand 3a is active for amination and Suzuki reactions using unactivated aryl iodides, bromides, or chlorides. Filtration of the catalyst from the reaction mixtures allows for simplified product isolation via an aqueous workup. The resin-bound catalyst can be recycled without additional palladium in both the amination and Suzuki reactions.
(DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination
Semeniuchenko, Volodymyr,Sharif, Sepideh,Day, Jonathan,Chandrasoma, Nalin,Pietro, William J.,Manthorpe, Jeffrey,Braje, Wilfried M.,Organ, Michael G.
, p. 10343 - 10359 (2021/07/31)
(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.
Nickel-Catalyzed Amination of Aryl Thioethers: A Combined Synthetic and Mechanistic Study
Bismuto, Alessandro,Delcaillau, Tristan,Müller, Patrick,Morandi, Bill
, p. 4630 - 4639 (2020/05/19)
Herein, we report a nickel-1,2-bis(dicyclohexylphosphino)ethane (dcype) complex for the catalytic Buchwald-Hartwig amination of aryl thioethers. The protocol shows broad applicability with a variety of different functional groups tolerated under the catalytic conditions. Extensive organometallic and kinetic studies support a nickel(0)-nickel(II) pathway for this transformation and revealed the oxidative addition complex as the resting state of the catalytic cycle. All the isolated intermediates have proven to be catalytically and kinetically competent catalysts for this transformation. The fleeting transmetalation intermediate has been successfully synthesized through an alternative synthetic organometallic pathway at lower temperature, allowing for in situ NMR study of the C-N bond reductive elimination step. This study addresses key factors governing the mechanism of the nickel-catalyzed Buchwald-Hartwig amination process, thus improving the understanding of this important class of reactions.