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

Hai-Long Lu; Fu-Hu Guo; Tong-Lin Wang; Xi-Cun Wang; Zheng-Jun Quan

doi:10.1055/s-0039-1690765

Synthesis, Table of Contents

Synthesis 2020; 52(06): 893-900
DOI: 10.1055/s-0039-1690765

paper

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

Authors

Hai-Long Lu

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China

^bGansu 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

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China

^bGansu 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

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China

^bGansu 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

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China

^bGansu 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∗

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China

^bGansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Lanzhou, Gansu 730070, P. R. of China Email: quanzhengjun@hotmail.com

Abstract

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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.

Keywords

C–S bond cleavage - arylboronic acids - alkynes - quinoline-2-thiones - Liebeskind–Srogl cross coupling

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References

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

Authors

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