Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings

Yuntong Zhai; Xiaofei Chen; Wei Zhou; Mengyang Fan; Yisheng Lai; Dawei Ma

doi:10.1021/acs.joc.7b00493

Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings

J Org Chem. 2017 May 5;82(9):4964-4969. doi: 10.1021/acs.joc.7b00493. Epub 2017 Apr 26.

Authors

Yuntong Zhai¹, Xiaofei Chen², Wei Zhou², Mengyang Fan², Yisheng Lai¹, Dawei Ma²

Affiliations

¹ State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.
² 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: 28427259
DOI: 10.1021/acs.joc.7b00493

Abstract

Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N'-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N'-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.

Publication types

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