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

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

› Author Affiliations

Abstract

All articles of this category

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

Full Text

References

References

1a Shang XF, Morris-Natschke SL, Liu YQ, Guo X, Xu XS, Goto M, Li JC, Yang GZ, Lee KH. Med. Res. Rev. 2018; 38: 775
1b Puri SC, Verma V, Amna T, Qazi GN, Spiteller M. J. Nat. Prod. 2005; 68: 1717

2 Tabassum S, Kumara TH. S, Jasinski JP, Millikan SP, Yathirajan HS, Ganapathy PS. S, Sowmya HB. V, More SS, Nagendrappa G, Kaur M, Jose G. J. Mol. Struct. 2014; 1070: 10
3 Kumar S, Kaushik D, Bawa S, Khan SA. Chem. Biol. Drug Des. 2012; 79: 104
4 El-Feky SA, Thabet HK, Ubeid MT. J. Fluorine Chem. 2014; 161: 87
5 Scott DA, Dakin LA, Daly K, Del Valle DJ, Diebold RB, Drew L, Ezhuthachan J, Gero TW, Ogoe CA, Omer CA, Redmond SP, Repik G, Thakur K, Ye Q, Zheng X. Bioorg. Med. Chem. Lett. 2013; 23: 4591

6a Li SM, Huang J, Chen GJ, Han FS. Chem. Commun. 2011; 47: 12840
6b Gothard CM, Soh S, Gothard NA, Kowalczyk B, Wei Y, Baytekin B, Grzybowski BA. Angew. Chem. Int. Ed. 2012; 51: 7922
6c Mitamura T, Ogawa A. J. Org. Chem. 2011; 76: 1163
6d Yaragorla S, Pareek A, Dada R, Saini PL. Eur. J. Org. Chem. 2017; 4600
6e Steib AK, Kuzmina OM, Fernandez S, Flubacher D, Knochel P. J. Am. Chem. Soc. 2013; 135: 15346
6f Ghorai J, Reddy AC. S, Anbarasan P. Chem. Asian J. 2018; 13: 2499
6g Zhang X, Xu X, Yu L, Zhao Q. Tetrahedron Lett. 2014; 55: 2280
6h Yamaguchi K, Noda T, Tomizawa T, Kanai E, Hioki H. Eur. J. Org. Chem. 2015; 4990
6i Xu X, Liu W, Wang Z, Feng Y, Yan Y, Zhang X. Tetrahedron Lett. 2016; 57: 226
6j Chen L.-C, Wang H.-M, Hou R.-S, Du H.-D, Kang I.-J. Heterocycles 2011; 83: 331
6k Tanwar B, Kumar D, Kumar A, Ansari MI, Qadri MM, Vaja MD, Singh M, Chakraborti AK. New J. Chem. 2015; 39: 9824
6l Park J, Park JS, Park YG, Lee JY, Kang JW, Liu J, Dai L, Jin S.-H. Org. Electron. 2013; 14: 2114
6m Das S, Maiti D, De Sarkar S. J. Org. Chem. 2018; 83: 2309
6n Jiang K.-M, Kang J.-A, Jin Y, Lin J. Org. Chem. Front. 2018; 5: 434
6o Sapkota K, Han SS. New J. Chem. 2017; 41: 5395
6p Ryabukhin SV, Naumchik VS, Plaskon AS, Grygorenko OO, Tolmachev AA. J. Org. Chem. 2011; 76: 5774
6q Das K, Mondal A, Srimani D. Chem. Commun. 2018; 54: 10582
6r Xiao F, Chen Y, Liu Y, Wang J. Tetrahedron 2008; 64: 2755
6s Wang Z, Zhang X, Liu W, Sun R, Xu X, Yan Y. Synlett 2016; 27: 1563
6t Cho H, Török F, Török B. Green Chem. 2014; 16: 3623

7a Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
7b Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
7c Korch KM, Watson DA. Chem. Rev. 2019; 119: 8192

8a Ben Halima T, Zhang W, Yalaoui I, Hong X, Yang Y.-F, Houk KN, Newman SG. J. Am. Chem. Soc. 2017; 139: 1311
8b Weires NA, Baker EL, Garg NK. Nat. Chem. 2016; 8: 75
8c Malapit CA, Bour JR, Brigham CE, Sanford MS. Nature 2018; 563: 100

9 Cui M, Wu H, Jian J, Wang H, Liu C, Daniel S, Zeng Z. Chem. Commun. 2016; 52: 12076

10a Zapf A. Angew. Chem. Int. Ed. 2003; 42: 5394
10b Kang FA, Sui Z, Murray WV. J. Am. Chem. Soc. 2008; 130: 11300
10c Liu C, Qin ZX, Ji CL, Hong X, Szostak M. Chem. Sci. 2019; 10: 5736

11a Maltsev OV, Rausch R, Quan Z.-J, Hintermann L. Eur. J. Org. Chem. 2014; 7426
11b Kim H, Phan NH. T, Shin H, Lee H.-S, Sohn J.-H. Tetrahedron 2017; 73: 6604
11c Ma Y, Cammarata J, Cornella J. J. Am. Chem. Soc. 2019; 141: 1918
11d Zapf A. Angew. Chem. 2003; 115: 5552

12 Li BJ, Yu DG, Sun CL, Shi ZJ. Chem. Eur. J. 2011; 17: 1728
13 Liebeskind LS, Srogl J. J. Am. Chem. Soc. 2000; 122: 11260
14 Lengar A, Kappe CO. Org. Lett. 2004; 6: 771

15a Cheng H.-G, Chen H, Liu Y, Zhou Q. Asian J. Org. Chem. 2018; 7: 490
15b Mehta VP, Sharma A, Eycken EV. B. Org. Lett. 2008; 10: 1147
15c Maltsev OV, Pöthig A, Hintermann L. Org. Lett. 2014; 16: 1282

16 Wang TL, Liu XJ, Huo CD, Wang XC, Quan ZJ. Chem. Commun. 2018; 54: 499

17a Quan Z.-J, Hu W.-H, Jia X.-D, Zhang Z, Da Y.-X, Wang X.-C. Adv. Synth. Catal. 2012; 354: 2939
17b Quan Z.-J, Lv Y, Jing F.-Q, Jia X.-D, Huo C.-D, Wang X.-C. Adv. Synth. Catal. 2014; 356: 325
17c Yan ZF, Quan ZJ, Da Y X, Zhang Z, Wang XC. Chem. Commun. 2014; 50: 13555
17d Du B.-X, Quan Z.-J, Da Y.-X, Zhang Z, Wang X.-C. Adv. Synth. Catal. 2015; 357: 1270
17e Yang Q, Quan Z, Du B, Wu S, Li P, Sun Y, Lei Z, Wang X. Catal. Sci. Technol. 2015; 5: 4522
17f Wang X.-C, Quan Z.-J, Liu M.-X, Gong H.-P. Synlett 2017; 29: 330

18a Savarin C, Srogl J, Liebeskind LS. Org. Lett. 2001; 3: 91
18b Liebeskind LS, Srogl J. Org. Lett. 2002; 4: 979
18c Kusturin CL, Liebeskind LS. Org. Lett. 2002; 4: 983
18d Lengar A, Kappe CO. Org. Lett. 2004; 6: 771
18e Villalobos JM, Srogl J, Liebeskind LS. J. Am. Chem. Soc. 2007; 129: 15734
18f Prokopcová H, Kappe CO. J. Org. Chem. 2007; 72: 4440

Supplementary Material

Supporting Information

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

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