613-36-5Relevant academic research and scientific papers
Mild and Selective Rhodium-Catalyzed Transfer Hydrogenation of Functionalized Arenes
Wang, Yuhan,Chang, Zhiqian,Hu, Yan,Lin, Xiao,Dou, Xiaowei
supporting information, p. 1910 - 1914 (2021/03/08)
Diboron-mediated rhodium-catalyzed transfer hydrogenation of functionalized arenes is reported. In addition to good functional group tolerance, the reaction features operational simplicity and controllable chemoselectivity. The general applicability of this procedure is demonstrated by the selective hydrogenation of a range of arenes, including functionalized benzenes, biphenyls, and polyaromatics.
Aryl or heteroaryl methoxylation reaction method
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Paragraph 0127-0133, (2021/11/21)
The invention discloses an aryl or heteroaryl methoxylation reaction method. The method comprises the following steps: preparing a substrate. The coupling agent, ligand, solvent, catalyst and base are mixed homogeneously in an inert gas to give the aryl or heteroaryl methoxy compounds. Compared with a methoxylation reaction method in the prior art, the method has the advantages that the reaction system conditions are mild, the usage amount of the catalyst and the ligand is low to 5% of the amount of the substrate material, and the catalytic efficiency is improved. The method has better compatibility to different substrate expansion and discovery of aryl halides or heteroaryl halides with different functional groups. The yield of aryl or heteroaryl methoxy compounds prepared by the method disclosed by the invention is 36% - 89%.
A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents
He, Xiao-Yun
, p. 823 - 832 (2021/07/19)
Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond. Graphic abstract: [Figure not available: see fulltext.].
Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling for C(sp2)-C(sp3) and C(sp3)-C(sp3) Bond Formation
Koh, Ming Joo,Wei, Yi,Yang, Tao
, p. 6519 - 6525 (2021/06/25)
The construction of C-C bonds through cross-coupling between two electrophiles in the absence of excess metallic reducing agents is a desirable objective in chemistry. Here, we show that N-alkylpyridinium salts can be efficiently merged with aryl or alkyl halides in an intermolecular fashion, affording products in up to 92% yield at ambient temperature. These reactions harness the ability of N-alkylpyridinium salts to form electron donor-acceptor complexes with Hantzsch esters, enabling photoinduced single-electron transfer and fragmentation to afford alkyl radicals that are subsequently trapped by a Ni-based catalytic species to promote C(sp2)-C(sp3) and C(sp3)-C(sp3) bond formation. The operationally simple protocol is applicable to site-selective cross-coupling and tolerates diverse functional groups, including those that are sensitive toward metal reductants.
Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling
Neate, Peter G.N.,Zhang, Bufan,Conforti, Jessica,Brennessel, William W.,Neidig, Michael L.
supporting information, p. 5958 - 5963 (2021/08/18)
Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.
Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation
Cao, Yuhui,Che, Jinteng,Chen, Han,Chen, Si-Cong,Fang, Xianhe,Guo, Yinliang,Guo, Zhixian,Kong, Lingran,Li, Chen,Lu, Jia-Tian,Luo, Tuoping,Zhang, Nan,Zhu, Qi
, p. 14046 - 14052 (2021/09/13)
A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.
Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe
Li, Chen,Song, Zhi-Qiang,Wang, Dong-Hui,Wang, Jing-Ru
supporting information, p. 8450 - 8454 (2021/11/17)
A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.
Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions
Doppiu, Angelino,Goo?en, Lukas J.,Hu, Zhiyong,Pirkl, Nico,Sivendran, Nardana
supporting information, p. 25151 - 25160 (2021/10/19)
Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.
Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts
Minami, Hiroko,Nogi, Keisuke,Yorimitsu, Hideki
, p. 1542 - 1546 (2021/09/06)
Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C-S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S -methylation with MeOTf. Mechanistic experiments suggest that C-S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C-S cleavage and radical recombination step.
Regiodivergent DH or HD Addition to Alkenes: Deuterohydrogenation versus Hydrodeuterogenation
Hilt, Gerhard,Li, Luomo
, (2020/03/03)
The regioselective and regiodivergent addition of H-D to a variety of 1,1-diarylalkenes was realized utilizing selectively deuterated dihydroaromatic compounds, which were generated by cobalt catalysis. The reaction was initiated by catalytic amounts of B
