Silver(I)-mediated oxidation/cyclization of acrylamides with alkyl trifluoroborates

Siyi Dinga , Huaping Rena, Min Zhua, Qiang Maa, Zongcheng Miaoa* & Pengfei Lib*a Xi'an Key Laboratory of Advanced Photo-electronics Materials and Energy Conversion Device, School of Science, Xijing University, Xi’an, Chinab Bioactive Small Molecules Research Group, Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an, ChinaSupplemental data for this article can be accessed on the publisher's website.CONTACT Zongcheng Miao miaozongcheng@xijing.edu.cn Xi'an Key Laboratory of Advanced Photo-electronics Materials and Energy Conversion Device, School of Science, Xijing University, Xi’an 710123, China; Pengfei Li lipengfei@mail.xjtu.edu.cn Bioactive Small Molecules Research Group, Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710049, China.AbstractA mild silver-mediated oxidative cyclization of acrylamides has been developed by using alkyl trifluoroborates as radical precursors. It proceeds through a tandem radical addition/cyclization process, in which two new carbon-carbon bonds were formed. This protocol allows reliable and practical access to build the skeleton of 3,3-disubstituted oxindoles in moderate yields, the readily available starting reagents, broad substrate scope and mild reaction conditions are the characteristic features of this protocol.