General rhodium-catalyzed oxidative cross-coupling reactions between anilines: synthesis of unsymmetrical 2,2′-diaminobiaryls

Abstract

Described herein is a dual chelation-assisted RhCl3-catalyzed oxidative C–H/C–H cross-coupling reaction of aniline derivatives, in which the chemo- and regioselective cross-coupling between electronically similar substrates is achieved.

Direct para-Selective C–H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

“…General Procedure for the Compound (1j−1ab). 23 A 100 mL round bottom flask was charged with aniline derivatives (20 mmol), CH 2 Cl 2 (40 mL) and Et 3 N (4.0 mL, 28 mmol). Then, the reaction solution was cooled to 0 °C.…”

Recent advances in rhodium-catalysed cross-dehydrogenative-coupling between two C(sp2)–H bonds

“…The RhCl 3 -catalysed CDC reaction of aniline derivatives for affording 2,2′-diaminobiaryls was further shown in 2019 (Scheme 45b). 64 With their former platform, an extended general CDC reaction between two anilines, between two phenols, and between phenols and anilines by employing a co-oxidant-free Rh( i )/Zn(NTf 2 ) 2 /air catalyst system was later reported (Scheme 45c & d). 65 A broad range of bisanilines, bisphenols and 2′-aminobiphenyl-2-ols were presented.…”

Structurally Nontraditional Benzo[c]cinnoline‐Based Electron‐Transporting Materials with 3D Molecular Interaction Architecture

“…[10] Recently, transition metal-catalyzed oxidative CÀ H/CÀ H coupling reactions have proven to be one of the most powerful tools to forge biaryl scaffolds, [11] which can not only avoid multiple and complicated prefunctionalizations in traditional CÀ X/CÀ M coupling reactions, but also tolerate halogens beneficial for further installation of functional groups. Inspired by our previous work on oxidative CÀ H/CÀ H coupling reactions between arenes, [12] we herein presented a streamlined synthetic route to rapidly construct DPBZC by using the rhodium-catalyzed CÀ H/CÀ H homocoupling reaction of N-([1,1'-biphenyl]-4-yl)acetamide and sequential ring closure of 2,2'-diaminobiaryls (Scheme 2). In addition, DMDPBZC was also designed with two methyl groups at the 4-and 7-positions of the BZC skeleton as a reference for insight into intermolecular interactions [13] and was prepared with N-(4-chloro-2-methylphenyl)pivalamide as the starting material, illustrating the utmost convenience of CÀ H activation in assembling organic functional molecules.…”