CoPc/Cu(OAc)2-catalyzed N-arylation of amines with arylhydrazines leading to N-aryl amines. Issue 41 (13th October 2016)

• Record Type: Journal Article
• Authors: Sun, Wang-Bin; Zhang, Pei-Zhi; Jiang, Tao; Li, Cheng-Kun; An, Li-Tao; Shoberu, Adedamola; Zou, Jian-Ping
• Is Part Of: Tetrahedron. Volume 72:Issue 41(2016)
• Page Start: 6477
• Page End: 6483
• Publication Date: 2016-10-13
• Subjects: Arylation -- Amine -- CoPc -- Catalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.08.058
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The N-arylation of amines with arylhydrazines has been developed, achieving the selective cross-coupling of aryl radicals with amines to form N -aryl amines. The reaction uses air as an oxidant, CoPc and Cu(OAc)2 as catalysts. The reaction proceeds under mild conditions in air through a relay process, arylhydrazines are oxidized to aryldiazenes by CoPc, further oxidized to aryl radicals by air (O2 ), which are trapped by Cu(OAc)2 –amine complex, followed by reduction–elimination reaction to form N -aryl amines. Arylamines and arylhydrazines give the highest yields, but N -aryl- N -alkylamines and N -alkylamines can be used as well. Graphical abstract: