Synthesis 2020; 52(06): 893-900
DOI: 10.1055/s-0039-1690765
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed/Copper-Mediated Desulfurization and Aryl­­ation of Quinoline-2-(1H)-thione for Rapid Access to Quinoline Derivatives

Hai-Long Lu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China
b   Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Lanzhou, Gansu 730070, P. R. of China   Email: quanzhengjun@hotmail.com
,
Fu-Hu Guo
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China
b   Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Lanzhou, Gansu 730070, P. R. of China   Email: quanzhengjun@hotmail.com
,
Tong-Lin Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China
b   Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Lanzhou, Gansu 730070, P. R. of China   Email: quanzhengjun@hotmail.com
,
Xi-Cun Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China
b   Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Lanzhou, Gansu 730070, P. R. of China   Email: quanzhengjun@hotmail.com
,
Zheng-Jun Quan
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China
b   Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Lanzhou, Gansu 730070, P. R. of China   Email: quanzhengjun@hotmail.com
› Author Affiliations
We are thankful for the financial support from the National Nature Science Foundation of China (No. 21562036), and the Key Talent Projects in Gansu Province (2018A-004).
Further Information

Publication History

Received: 21 September 2019

Accepted after revision: 26 November 2019

Publication Date:
09 December 2019 (online)


Abstract

An efficient method for carbon–carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1H)-thiones with arylboronic acids or alkynes through C–S bond cleavage without an inert atmosphere. The method provides rapid and general access to a diverse range of 2-substituted quinolines in a single step from a wide range of quinoline-2-(1H)-thiones and arylboronic acids or alkynes.

Supporting Information