Synthesis of N-(2-pyridyl)indoles via Pd(II)-catalyzed oxidative coupling

Jinlei Chen; Qingyu Pang; Yanbo Sun; Xingwei Li

doi:10.1021/jo1025546

Synthesis of N-(2-pyridyl)indoles via Pd(II)-catalyzed oxidative coupling

J Org Chem. 2011 May 6;76(9):3523-6. doi: 10.1021/jo1025546. Epub 2011 Mar 22.

Authors

Jinlei Chen¹, Qingyu Pang, Yanbo Sun, Xingwei Li

Affiliation

¹ State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130023, People's Republic of China.

PMID: 21417495
DOI: 10.1021/jo1025546

Abstract

Readily available Pd(II) chloride catalysts can catalyze selective and efficient oxidative coupling between N-aryl-2-aminopyridines and internal alkynes to yield N-(2-pyridyl)indoles. This process involves the ortho C-H activation of N-aryl-2-aminopyridines, and CuCl(2) was used as an oxidant. Compared to our previously reported Rh(III)-catalyzed synthesis of this class of product, this method is advantageous with a wider scope of alkynes and cost-effective Pd(II) catalysts. Molecular oxygen can be used as a terminal oxidant.