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N ‐(4‐Thiazolylmethyl)Morpholine N ‐Oxide as N,O‐Bidentate Ligand for Copper‐Catalyzed Ullmann‐Type N‐Arylation of Azoles/Amines with Aryl Halides
Author(s) -
Jia Xuefeng,
Peng Pai
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900273
Subject(s) - morpholine , chemistry , denticity , aryl , catalysis , halide , ligand (biochemistry) , medicinal chemistry , ullmann reaction , copper , combinatorial chemistry , organic chemistry , metal , biochemistry , alkyl , receptor
An effective and practical protocol for the CuI‐catalyzed Ullmann‐type N‐arylation of azoles/amines with aryl halides is reported. The key strategy is the employment of CH 2 linker N,O‐bidentate ligands, especially N ‐(4‐thiazolylmethyl)morpholine N ‐oxide, as superior supporting ligands. The highly efficient C−N coupling reactions between various azoles/amines and aryl halides bearing different functional groups can be achieved under CuI/N‐(4‐thiazolylmethyl)morpholine N‐oxide catalytic system, affording a variety of N‐arylated products. The use of cheap copper(I) salt and readily available N,O‐bidentate ligands make this procedure more attractive for synthesis of valuable functionalized nitrogen‐containing heterocyclic compounds.