title: Copper/B2pin2-catalyzed C-H difluoroacetylation-cycloamidation of anilines leading to the formation of 3,3-difluoro-2-oxindoles.
abstract: An original and efficient synthesis of 3,3-difluoro-2-oxindole derivatives has been developed via copper/B2pin2-catalyzed difluoroacetylation of aniline via C-H activation followed by intramolecular amidation. In this method, amino groups in primary, secondary or tertiary anilines act as directing groups, providing ortho-difluoroacetylated products regioselectively. And in the first two cases, further intramolecular amidation affords 3,3-difluoro-2-oxindole derivatives via a one-pot strategy. This method facilitates the synthesis of compound A as a potent and selective EP3receptor antagonist in only five steps in 13% yield instead of the previously reported nine steps in overall 4% yield.
authors.affiliation: Institute of Next Generation Matter Transformation, College of Chemical Engineering at Huaqiao University, P. R. China. qsong@hqu.edu.cn and College of Materials Science & Engineering at Huaqiao University, Xiamen, Fujian 361021, P. R. China.
authors.forename: Miaolin
authors.initials: M
authors.lastname: Ke
authors.affiliation: Institute of Next Generation Matter Transformation, College of Chemical Engineering at Huaqiao University, P. R. China. qsong@hqu.edu.cn.
authors.forename: Qiuling
authors.identifier: http://orcid.org/0000-0002-9836-8860
authors.initials: Q
authors.lastname: Song