A carboxylate-assisted amination/unactivated C(sp2)-H arylation reaction via a palladium/norbornene cooperative catalysis

Yang An; Bo-Sheng Zhang; Zhe Zhang; Ce Liu; Xue-Ya Gou; Ya-Nan Ding; Yong-Min Liang

doi:10.1039/c9cc09265j

A carboxylate-assisted amination/unactivated C(sp²)-H arylation reaction via a palladium/norbornene cooperative catalysis

Chem Commun (Camb). 2020 Jun 4;56(44):5933-5936. doi: 10.1039/c9cc09265j. Epub 2020 Apr 28.

Authors

Yang An¹, Bo-Sheng Zhang, Zhe Zhang, Ce Liu, Xue-Ya Gou, Ya-Nan Ding, Yong-Min Liang

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China. liangym@lzu.edu.cn.

PMID: 32342950
DOI: 10.1039/c9cc09265j

Abstract

This report describes a carboxylate-assisted palladium-catalysed Catellani reaction, which is compatible with ortho-amination and unactivated C(sp²)-H arylation. This method was used to synthesize a series of 1-amino substituted dihydrophenanthridines, phenanthridines and 6H-benzo[c]chromenes. Based on kinetic isotope experiments, the kinetic curve proves that pivalic acid accelerates the reaction rate of unactivated C(sp²)-H activation, and thus this rate can keep up with the five membered aryl-norbornene-palladacycle (ANP) intermediate.