N,N'-Bisoxalamides Enhance the Catalytic Activity in Cu-Catalyzed Coupling of (Hetero)Aryl Bromides with Anilines and Secondary Amines.

doi:10.1021/acs.joc.7b02363

Paper

N,N'-Bisoxalamides Enhance the Catalytic Activity in Cu-Catalyzed Coupling of (Hetero)Aryl Bromides with Anilines and Secondary Amines.

Published Nov 16, 2017 · Subhajit Bhunia, S. Kumar, D. Ma

The Journal of organic chemistry

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28

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Abstract

N,N'-Bis(furan-2-ylmethyl)oxalamide (BFMO), an inexpensive and conveniently available bidentate ligand, is very effective for promoting Cu-catalyzed N-arylation of anilines and cyclic secondary amines. The method enables coupling of a broad range of (hetero)aryl bromides with various (hetero)aryl amines and cyclic secondary amines at 0.5-5 mol % catalyst loadings at relatively low temperatures. For coupling with more sterically hindered acyclic secondary amines, using N,N'-bis(2,4,6-trimethoxyphenyl)oxalamide (BTMPO) as a ligand gives the better results. Additionally, high selectivity is achieved in CuI/BFMO-catalyzed direct monoarylation of piperazine with (hetero)aryl bromides to afford pharmaceutically important building blocks.

Study Snapshot

N,N'-Bis(furan-2-ylmethyl)oxalamide (BFMO) enhances the catalytic activity in Cu-catalyzed N-arylation of anilines and cyclic secondary amines, enabling the coupling of various (hetero)aryl bro

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

N,N'-Bisoxalamides Enhance the Catalytic Activity in Cu-Catalyzed Coupling of (Hetero)Aryl Bromides with Anilines and Secondary Amines.

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