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

  • J Org Chem. 2017 Dec 1;82(23):12603-12612. doi: 10.1021/acs.joc.7b02363.
Subhajit Bhunia  1 ,  S Vijay Kumar  1 ,  Dawei Ma  1
Affiliations
  • 1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
PMID: 29117476 DOI: 10.1021/acs.joc.7b02363
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.

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