35488-09-6Relevant articles and documents
Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis
Zhou, Chao,Lei, Tao,Wei, Xiang-Zhu,Ye, Chen,Liu, Zan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 16805 - 16813 (2020/11/09)
Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.
Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
Moser, Daniel,Duan, Yaya,Wang, Feng,Ma, Yuanhong,O'Neill, Matthew J.,Cornella, Josep
, p. 11035 - 11039 (2018/07/31)
The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C?N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C?O, C?N, C?S, or C?SO2R bonds are disclosed herein. In contrast to C?N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional-group tolerance. In addition to small-molecule derivatization, Pyry-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.
New stable Cu(I) catalyst supported on weakly acidic polyacrylate resin for green C-N coupling: Synthesis of N-(Pyridin-4-yl)benzene amines and N,N-Bis(pyridine-4-yl)benzene amines
Kore, Nitin,Pazdera, Pavel
, (2017/01/24)
A method for preparation of a new stable Cu(I) catalyst supported on weakly acidic polyacrylate resin without additional stabilizing ligands is described. A simple and efficient methodology for Ullmann Cu(I) catalyzed C-N cross coupling reactions using this original catalyst is reported. Coupling reactions of 4-chloropyridinium chloride with anilines containing electron donating (EDG) or electron withdrawing (EWG) groups, naphthalen-2-amine and piperazine, respectively, are successfully demonstrated.