53451-88-0Relevant articles and documents
General Paradigm in Photoredox Nickel-Catalyzed Cross-Coupling Allows for Light-Free Access to Reactivity
Nocera, Daniel G.,Qin, Yangzhong,Sun, Rui
, p. 9527 - 9533 (2020)
Self-sustained NiI/III cycles are established as a potentially general paradigm in photoredox Ni-catalyzed carbon–heteroatom cross-coupling reactions through a strategy that allows us to recapitulate photoredox-like reactivity in the absence of light across a wide range of substrates in the amination, etherification, and esterification of aryl bromides, the latter of which has remained, hitherto, elusive under thermal Ni catalysis. Moreover, the accessibility of esterification in the absence of light is especially notable because previous mechanistic studies on this transformation under photoredox conditions have unanimously invoked energy-transfer-mediated pathways.
Light-Promoted C–N Coupling of Aryl Halides with Nitroarenes
Li, Gang,Yang, Liu,Liu, Jian-Jun,Zhang, Wei,Cao, Rui,Wang, Chao,Zhang, Zunting,Xiao, Jianliang,Xue, Dong
supporting information, p. 5230 - 5234 (2021/02/05)
A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate.
A Unified and Practical Method for Carbon–Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis
Escobar, Randolph A.,Johannes, Jeffrey W.
supporting information, (2020/04/17)
While carbon–heteroatom cross-coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C?O, C?N and C?S cross-coupling reactions under one general set of conditions. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel(II) complex, is responsible for the key reductive elimination step that couples aryl bromides, iodides, and chlorides to 1° and 2° alcohols, amines, thiols, carbamates, and sulfonamides, and is amenable to scale up via a flow apparatus.
