192461-90-8Relevant articles and documents
Catalytic Amination of Phenols with Amines
Chen, Kai,Kang, Qi-Kai,Li, Yuntong,Wu, Wen-Qiang,Zhu, Hui,Shi, Hang
supporting information, p. 1144 - 1151 (2022/02/05)
Given the wide prevalence and ready availability of both phenols and amines, aniline synthesis through direct coupling between these starting materials would be extremely attractive. Herein, we describe a rhodium-catalyzed amination of phenols, which provides concise access to diverse anilines, with water as the sole byproduct. The arenophilic rhodium catalyst facilitates the inherently difficult keto–enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. We demonstrate the generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines. Several examples of late-stage functionalization of structurally complex bioactive molecules, including pharmaceuticals, further illustrate the potential broad utility of the method.
Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines
Chen, Zhengwang,Zeng, Huiying,Gong, Hang,Wang, Haining,Li, Chao-Jun
, p. 4174 - 4178 (2015/06/25)
Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and tertiary substituted cyclohexylamines can be synthesized under convenient conditions in moderate to excellent yields.
Palladium-catalyzed asymmetric hydrogenation of simple ketimines using a Bronsted acid as activator
Zhou, Xiao-Yu,Bao, Ming,Zhou, Yong-Gui
supporting information; experimental part, p. 84 - 88 (2011/03/23)
Using a catalytic amount of a Bronsted acid as activator of simple imines, the highly enantioselective homogeneous palladium-catalyzed asymmetric hydrogenation of simple ketimines was successfully developed with up to 95% ee.