56153-61-8Relevant academic research and scientific papers
Nitrile Synthesis via Desulfonylative-Smiles Rearrangement
Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi
, p. 4460 - 4467 (2022/03/15)
Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.
Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides
Chan, Cheng-Lin,Hsu, Che-Ming,Lee, Shao-Chi,Li, Li-Yun,Liao, Hsuan-Hung,Mi?oza, Shinje,Tsai, Hao-En,Tsai, Zong-Nan,Tsao, Yong-Ting
, (2022/02/07)
The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.
Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst
Antonietti, Markus,Ghosh, Indrajit,K?nig, Burkhard,Khamrai, Jagadish,Savateev, Aleksandr
, p. 3526 - 3532 (2020/04/09)
The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-co
Preparation method of o-amino diphenylmethane
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Paragraph 0017; 0028; 0030; 0034; 0036; 0040; 0042; 0046, (2019/09/17)
The invention relates to a preparation method of o-amino diphenylmethane, and belongs to the technical field of pharmaceutical synthesis. The preparation method comprises steps as follows: o-cyano-diphenylmethane is prepared from o-cyanobenzyl chloride and benzene through a reaction, then o-cyano-diphenylmethane is hydrolyzed in an aqueous solution of ethanediol, o-amide-diphenylmethane is obtained and is subjected to a rearrangement reaction with sodium hypochlorite, reduced-pressure distillation is performed, and o-amino diphenylmethane is obtained. O-amino diphenylmethane prepared with themethod is high in yield, the yield can reach 89% or above, meanwhile, a finished o-amino diphenylmethane product is high in purity, the purity can reach 99% or above, product quality is good, and defects of low purity and low yield of the product prepared with a traditional method are overcome. Besides, the preparation method is simple to operate and needs few steps, impurities in the product areeasy to separate and remove, and large-scale industrial production is facilitated.
Cobalt-Catalyzed Formation of Functionalized Diarylmethanes from Benzylmesylates and Aryl Halides
Reddy, Bhoomireddy Rajendra Prasad,Chowdhury, Sushobhan,Auffrant, Audrey,Gosmini, Corinne
, p. 3026 - 3029 (2018/08/24)
A simple cobalt-catalyzed reductive coupling protocol allowing the synthesis of functionalized diarylmethanes from benzyl mesylate is described. The possibility to directly use the benzyl alcohol as a result of a two-step reaction is also presented. This method tolerates a variety of functional groups. A benzyl radical is likely involved. (Figure presented.).
Synthesis of bench-stable solid triorganoindium reagents and reactivity in palladium-catalyzed cross-coupling reactions
Gil-Negrete, José M.,Pérez Sestelo, José,Sarandeses, Luis A.
supporting information, p. 1453 - 1456 (2018/02/19)
Bench-stable solid triorganoindium compounds have been prepared by coordination with 4-(dimethylamino)pyridine (DMAP). The solid R3In(DMAP) complexes are obtained from the corresponding solution of R3In in quantitative yield and can
Radical-Based C?C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines
Buzzetti, Luca,Prieto, Alexis,Roy, Sudipta Raha,Melchiorre, Paolo
supporting information, p. 15039 - 15043 (2017/11/20)
We report herein that 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) can directly reach an electronically excited state upon light absorption and trigger the generation of C(sp3)-centered radicals without the need for an external photocatalyst. Selective excitation with a violet-light-emitting diode turns alkyl-DHPs into strong reducing agents that can activate reagents through single-electron transfer manifolds while undergoing homolytic cleavage to generate radicals. We used this photochemical dual-reactivity profile to trigger radical-based carbon–carbon bond-forming processes, including nickel-catalyzed cross-coupling reactions.
Visible-Light-Mediated Aromatic Substitution Reactions of Cyanoarenes with 4-Alkyl-1,4-dihydropyridines through Double Carbon-Carbon Bond Cleavage
Nakajima, Kazunari,Nojima, Sunao,Sakata, Ken,Nishibayashi, Yoshiaki
, p. 1028 - 1032 (2016/04/05)
Novel aromatic substitution reactions of cyanoarenes with 4-alkyl-1,4-dihydropyridines as alkylating reagents in the presence of a catalytic amount of a photoredox catalyst proceed smoothly to give the corresponding alkyl-substituted arenes in good to high yields. The present reaction system realizes a novel C-C bond-forming reaction between two fragments generated from the C-C bond-cleavage reactions of two independent substrates.
Cobalt-Catalyzed Reductive Cross-Coupling Between Benzyl Chlorides and Aryl Halides
Pal, Suman,Chowdhury, Sushobhan,Rozwadowski, Elodie,Auffrant, Audrey,Gosmini, Corinne
supporting information, p. 2431 - 2435 (2016/08/16)
A new protocol for the direct reductive cobalt-catalyzed arylation of benzyl chlorides has been developed in order to form functionalized diarylmethanes. A variety of reactive groups either on the aryl or the benzyl halide was employed. This represents the first cobalt-catalyzed reductive cross-coupling which does not require any ligand and pyridine. A reaction pathway is proposed involving a radical benzyl species. (Figure presented.).
Efficient synthesis of diarylmethane derivatives by PdCl2 catalyzed cross-coupling reactions of benzyl chlorides with aryl boronic acids in aqueous medium
Zhao, Guangkuan,Zhang, Kena,Wang, Liang,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, p. 6700 - 6703 (2016/02/03)
The research provides a simple and efficient method for preparing diarylmethane derivatives using the cross-coupling reaction of benzyl chlorides and aryl boronic acids catalyzed by palladium chloride in DMF aqueous solution without additional ligand.
