Nickel-Catalyzed Reductive Cross-Coupling of (Hetero)Aryl Iodides with Fluorinated Secondary Alkyl Bromides

• DOI: 10.1021/acs.orglett.5b02716
• Publication Date: 2015-10-29T18:10:19Z
• Authors: Xuefei Li; Zhang Feng; Zhong-Xing Jiang; Xingang Zhang
• Keywords: Fluorine; Functional group; Coupling reaction

A mild and efficient nickel-catalyzed reductive cross-coupling between fluorinated secondary alkyl bromides (hetero)aryl iodides is described. The use of FeBr2 as an additive successfully overcomes the hydrodebromination β-fluorine elimination substrates allows synthesis a wide range trifluoromethyl difluoroalkyl containing aliphatic compounds with fluoroalkyl substituted tertiary carbon center. notable features this protocol are synthetic operational simplicity without preparation moisture sensitive organometallic reagents excellent functional group compatibility, even toward active proton substrates.