Direct one-pot synthesis of primary 4-amino-2,3-diaryl-quinolines via Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodoquinolines with arylboronic acids

Malose Jack Mphahlele; Mamasegare Mabel Mphahlele

doi:10.3390/molecules16118958

Direct one-pot synthesis of primary 4-amino-2,3-diaryl-quinolines via Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodoquinolines with arylboronic acids

Molecules. 2011 Oct 25;16(11):8958-72. doi: 10.3390/molecules16118958.

Authors

Malose Jack Mphahlele¹, Mamasegare Mabel Mphahlele

Affiliation

¹ Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. mphahmj@unisa.ac.za

Abstract

Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodo-quinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism, which implicates palladium hydride species in the reduction of the incipient 2,3-diaryl-4-azidoquinolines to afford the 4-amino-2,3-diarylquinolines is proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Boronic Acids / chemistry*
Catalysis
Molecular Structure
Palladium / chemistry
Quinolines / chemical synthesis*
Quinolines / chemistry*

Substances

Boronic Acids
Quinolines
palladium hydride
Palladium