Weak coordinated nitrogen functionality enabled regioselective C-H alkynylation via Pd(II)/mono- N-protected amino acid catalysis

Bifu Liu; Wensen Ouyang; Jianhong Nie; Yang Gao; Kejun Feng; Yanping Huo; Qian Chen; Xianwei Li

doi:10.1039/d0cc04739b

Weak coordinated nitrogen functionality enabled regioselective C-H alkynylation via Pd(II)/mono- N-protected amino acid catalysis

Chem Commun (Camb). 2020 Sep 24;56(76):11255-11258. doi: 10.1039/d0cc04739b.

Authors

Bifu Liu¹, Wensen Ouyang², Jianhong Nie², Yang Gao², Kejun Feng¹, Yanping Huo², Qian Chen², Xianwei Li²

Affiliations

¹ School of Chemistry and Material Engineering, Huizhou University, Huizhou, 516007, China.
² School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, China. xwli@gdut.edu.cn.

PMID: 32820769
DOI: 10.1039/d0cc04739b

Abstract

The exploration of weak coordinated amine derivative enabled regioselective C-H functionalization remains challenging due to the elusive achievement of reactivity and selectivity simultaneously. Herein, regioselective C-H alkynylation of various readily transformable nitrogen functionalities was developed with great efficiency, with the assistance of the mono-N-protected amino acid (MPAA) ligand via Pd(ii) catalysis proceeding via 5, 6 and 7-membered palladacycle intermediates.