文献类型：期刊文献

英文题名：Skeletal Reconstruction of 3-Alkylidenepyrrolidines to Azepines Enabled by Pd-Catalyzed C-N Bond Cleavage

作者：Wu, Licheng[1,2];Wang, Tong[1,2];Gao, Chenyang[1,2];Huang, Wenyi[1,2];Qu, Jingping[1,2];Chen, Yifeng[1,2]

机构：[1]East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn, Key Lab Adv Mat,Feringa Nobel Prize Scientist Joi, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn, Joint Int Res Lab Precis Chem & Mol Engn,Feringa, Shanghai 200237, Peoples R China

年份：2021

卷号：11

期号：3

起止页码：1774

外文期刊名：ACS CATALYSIS

收录：;EI(收录号：20210609880865);WOS:【SCI-EXPANDED(收录号:WOS:000618540300058)】；

基金：This work was supported by NSFC/China (21702060), Shanghai Rising-Star Program, Shanghai Municipal Science and Technology Major Project (Grant No. 2018SHZDZX03) and the Program of Introducing Talents of Discipline to Universities (B16017), and the Fundamental Research Funds for the Central Universities. Y.C. thanks Dr. Aneta Turlik (UCLA) for helpful discussion during preparation of this manuscript. The authors thank Research Center of Analysis and Test of East China University of Science and Technology for the help on NMR analysis.

语种：英文

外文关键词：C-N cleavage; pyrrolidine; azepine; palladium; 1,5-dipole

摘要：Herein we report a Pd-catalyzed C-N bond cleavage strategy for the cycloaddition of pyrrolidines with azlactones or butenolides to construct the azepines. Leverage of the readily accessible 3-alkylidenepyrrolidine can serve as an effective precursor for zwitterionic salts. The in situ formation of an allyl-palladium intermediate through the cleavage of inert, cyclic C-N bonds leads to a cascade [5 + 2] cycloaddition, which allows for the diverse synthesis of azepine scaffolds with good functional group tolerance and 100% atom economy.