343864-48-2Relevant academic research and scientific papers
Gold-catalyzed Cycloisomerization of 2-Aryl-2-(arylamino)-3-butyn-1-ols toward 2-(2′-Aminoaryl)-2,5-dihydrofurans
Yang, Jianlin,Wu, Yuanhua,Zhang, Ming,Zhu, Dunru,Shen, Ruwei
, p. 2043 - 2048 (2018)
An interesting and highly selective gold-catalyzed cycloisomerization of 2-aryl-2-(arylamino)-3-butyn-1-ols to afford 2-(2′-aminoaryl)-2,5-dihydrofurans has been reported. The reaction is atom economic and highly efficient, and tolerates many functional groups including the cyano and allyl groups. A plausible mechanism for this new cycloismerization is also proposed. (Figure presented.).
Synthesis of Symmetric Bis(N-alkylaniline)triarylmethanes via Friedel-Crafts-Catalyzed Reaction between Secondary Anilines and Aldehydes
Gomes, Rafael F. A.,Coelho, Jaime A. S.,Frade, Raquel F. M.,Trindade, Alexandre F.,Afonso, Carlos A. M.
, p. 10404 - 10411 (2015)
The first general protocol for the preparation of symmetric triarylmethanes bearing secondary anilines by ytterbium-catalyzed Friedel-Crafts reaction of hetero(aryl) aldehydes and secondary anilines is reported. Mechanistic studies indicated that the imin
A convenient method for the Ru(0)-catalyzed regioselective deuteration of N-alkyl-substituted anilines
Zhan, Miao,Jiang, Hongxia,Pang, Xuehai,Zhang, Tao,Xu, Ruixue,Zhao, Lifeng,Liu, Yu,Gong, Yu,Chen, Yuanwei
, p. 5070 - 5073 (2014)
A highly effective and operationally practical method for the regioselective deuteration of N-alkyl-substituted anilines employing Ru3(CO)12(≤1 mol %) as catalyst and D2O as deuterium source was described. A variety of N-a
Silver-catalyzed regioselective deuteration of (hetero)arenes and α-deuteration of 2-alkyl azaarenes
Cong, Xuefeng,Dong, Baobiao,Hao, Na
, p. 25475 - 25479 (2020/07/28)
A simple silver-catalyzed regioselective deuteration of (hetero)arenes and α-deuteration of 2-alkyl azaarenes has been described. This strategy provides an efficient and practical avenue to access various deuterated electron-rich arenes, azaarenes and α-d
A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles
Zhou, Shuguang,Wang, Jinhu,Zhang, Feifei,Song, Chao,Zhu, Jin
supporting information, p. 2427 - 2430 (2016/06/09)
A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.
Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles
Zhou, Shuguang,Wang, Jinhu,Wang, Lili,Chen, Kehao,Song, Chao,Zhu, Jin
supporting information, p. 3806 - 3809 (2016/08/16)
A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.
Rhodium(III)-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate for cycloaddition/fragmentation synthesis of indazoles
Chen, Jinsen,Chen, Pei,Song, Chao,Zhu, Jin
supporting information, p. 14245 - 14249 (2015/02/05)
RhIII-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate allows subsequent construction of indazoles, a privileged heterocycle scaffold in synthetic chemistry, through the exploitation of reactivity between the directing group and installed group. The formal [2+2] cycloaddition/fragmentation reaction pathway identified herein, a unique reactivity pattern hitherto elusive for the N-nitroso group, emphasizes the importance of forward reactivity analysis in the development of useful C-H functionalization-based synthetic tools. The synthetic utility of the protocol is demonstrated with the synthesis of a tri-cyclic-fused ring system. The diversity of covalent linkages available for the nitroso group should enable the extension of the genre of reactivity reported herein to the synthesis of other types of heterocycles.
Microwave mediated hydrogen deuterium exchange: A rapid synthesis of 2H-substituted benzimidazole
Vaidyanathan, Srirajan,Surber, Bruce W.
, p. 5195 - 5197 (2007/10/03)
Deuterium aromatic substituted compounds were prepared by microwave irradiation of the parent unlabeled compounds in the presence of deuterium oxide and deuterium chloride. The percentage of deuterium incorporation was investigated under various reaction
Mechanism of Diazo Coupling Reactions. Part XXXII. The Diazoamino Rearrangement in 20percent Acetonitrile/Aqueous Buffers
Kelly, Richard P.,Penton, John R.,Zollinger, Heinrich
, p. 122 - 132 (2007/10/02)
The rearrangements of 4'-methoxy-N-methyl- and N-methyl-4'-nitro-diazoaminobenzene have been studied in 20percent acetonitrile/aqueous buffers.The reactions are specifically acid catalyzed and involve pre-equilibrium formation of amine and diazonium salt
