Cu/ N, N'-Dibenzyloxalamide-Catalyzed N-Arylation of Heteroanilines

Zhixiang Chen; Dawei Ma

doi:10.1021/acs.orglett.9b02509

Cu/ N, N'-Dibenzyloxalamide-Catalyzed N-Arylation of Heteroanilines

Org Lett. 2019 Sep 6;21(17):6874-6878. doi: 10.1021/acs.orglett.9b02509. Epub 2019 Aug 15.

Authors

Zhixiang Chen¹, Dawei Ma¹

Affiliation

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Science, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 31414821
DOI: 10.1021/acs.orglett.9b02509

Abstract

N,N'-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol % CuBr and 10 mol % DBO. For (hetero)aryl bromides/iodides, coupling reaction took place at 80-100 °C with 1 mol % CuI and 2 mol % DBO. A variety of heteroanilines worked well to afford the arylation products in good to excellent yields.

Publication types

Research Support, Non-U.S. Gov't