Synthesis, Table of Contents Synthesis 2022; 54(02): 475-482DOI: 10.1055/a-1645-6040 paper Synthesis of Aryl Dithiocarbamates from Tetramethylthiuram Monosulfide (TMTM) and Aryl Boronic Acids: Copper-Catalyzed Construction of C(sp2)–S Bonds Xu-Ling Xia‡ a School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China , Qi-Long Zhu‡ a School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China , Jin-Quan Chen a School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China , Zhen Shi b Hubei Key Laboratory of Biologic Resources Protection and Utilization, Hubei Minzu University, Enshi 445000, P. R. of China , Zhi-Bing Dong ∗ a School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China b Hubei Key Laboratory of Biologic Resources Protection and Utilization, Hubei Minzu University, Enshi 445000, P. R. of China c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, P. R. of China d Key Laboratory of Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430205, P. R. of China › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract A highly efficient method for the synthesis of S-aryl dithiocarbamates is reported. By using tetramethylthiuram monosulfide (TMTM) and aryl boronic acids as starting materials, C(sp2)–S bond-forming reactions proceed smoothly to give the desired aryl dithiocarbamates in good to excellent yields. The methodology features a simple procedure, broad functional group tolerance and excellent yields, whilst showing potential synthetic value for the preparation of a diverse range of biologically and pharmaceutically active compounds. Key words Key wordsdithiocarbamates - tetramethylthiuram monosulfide - boronic acids - organosulfur - copper Full Text References References 1a Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 283 1b Liu X, Dong ZB. Eur. J. Org. Chem. 2020; 408 1c Peng K, Zhu H, Liu X, Peng HY, Chen JQ, Dong ZB. Eur. J. Org. Chem. 2019; 7629 1d Peng K, Dong ZB. Adv. Synth. Catal. 2021; 363: 1 1e Chen JQ, Li JH, Dong ZB. Adv. Synth. Catal. 2020; 16: 3311 1f Peng K, Dong ZB. Eur. J. Org. Chem. 2020; 5488 1g Wu XM, Yan GB. Synlett 2019; 30: 610 1h Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457 1i Suzuki A. J. Organomet. Chem. 1999; 576: 147 1j Wu ZM, Li YC, Ding WZ, Zhu T, Liu SZ, Ren XH, Zou LH. Asian J. Org. Chem. 2016; 5: 625 1k Zou LH, Zhao C, Li PG, Wang Y, Li J. J. Org. Chem. 2017; 82: 12892 2a Amiri K, Rostami A, Samadi S, Rostami A. Catal. Commun. 2016; 86: 108 2b Basauri-Molina M, Hernández-Ortega S, Morales-Morales D. Eur. J. Inorg. Chem. 2014; 4619 2c Blank L, Fagnoni M, Protti S, Rueping M. Synthesis 2019; 51: 1243 2d Kanemoto K, Yoshida S, Hosoya T. Chem. Lett. 2018; 47: 85 2e Moghaddam FM, Pourkaveh R, Gholamtajari M. Appl. Organomet. Chem. 2018; 32: e4568 2f Movassagh B, Takallou A, Mobaraki A. J. Mol. Catal. A: Chem. 2015; 401: 55 3a Bhowmik A, Yadav M, Fernandes RA. Org. Biomol. Chem. 2020; 18: 2447 3b Dutta S, Saha A. Org. Biomol. Chem. 2019; 17: 9360 3c Hong B, Lee J, Lee A. Tetrahedron Lett. 2017; 58: 2809 3d Kapanda CN, Masquelier J, Labar G, Muccioli GG, Poupaert JH, Lambert DM. J. Med. Chem. 2012; 55: 5774 3e Kotali E, Varvoglis A. J. Chem. Soc., Perkin Trans. 1 1987; 2759 3f Liu Y, Lam LY, Ye J, Blanchard N, Ma C. Adv. Synth. Catal. 2020; 362: 2326 3g Sikari R, Sinha S, Das S, Saha A, Chakraborty G, Mondal R, Paul ND. J. Org. Chem. 2019; 84: 4072 3h Singh R, Allam BK, Singh N, Kumari K, Singh SK, Singh KN. Adv. Synth. Catal. 2015; 357: 1181 4a Ghorbani-Choghamarani A, Seydyosefi Z, Tahmasbi B. Appl. Organomet. Chem. 2018; 32: e4396 4b Kamal A, Srinivasulu V, Murty JN. S. R. C, Shankaraiah N, Nagesh N, Srinivasa Reddy T, Subba Rao AV. Adv. Synth. Catal. 2013; 355: 2297 4c Khakyzadeh V, Rostami A, Veisi H, Shirmardi Shaghasemi B, Reimhult E, Luque R, Xia Y, Darvishi S. Org. Biomol. Chem. 2019; 17: 4491 4d Li X, Mai S, Li X, Xu J, Xu H, Song Q. Org. Lett. 2020; 22: 7874 4e Tber Z, Hiebel MA, El Hakmaoui A, Akssira M, Guillaumet G, Berteina-Raboin S. RSC Adv. 2016; 6: 72030 4f Vatandoust Namanloo A, Akhlaghinia B, Mohammadinezhad A. J. Sulfur Chem. 2020; 41: 446 4g Wagner AM, Sanford MS. J. Org. Chem. 2014; 79: 2263 5a Bhadra S, Saha A, Ranu BC. Green Chem. 2008; 10: 1224 5b Chatterjee T, Bhadra S, Ranu BC. Green Chem. 2011; 13: 1837 5c Qi C, Guo T, Xiong W. Synlett 2016; 27: 2626 6a Jen K, Cava MP. Tetrahedron Lett. 1982; 23: 2001 6b Krasovskiy A, Gavryushin A, Knochel P. Synlett 2005; 2691 6c Krasovskiy A, Gavryushin A, Knochel P. Synlett 2006; 792 6d Grunwell JR. J. Org. Chem. 1970; 35: 1500 6e Krasovskiy A, Malakhov V, Gavryushin A, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040 6f Gronowitz S, Hornfeldt AB, Temciuc M. Synthesis 1993; 483 7a Dong ZB, Liu X, Bolm C. Org. Lett. 2017; 19: 5916 7b Cao Q, Peng HY, Cheng Y, Dong ZB. Synthesis 2018; 50: 1527 8 Xu W, Gao F, Dong ZB. Eur. J. Org. Chem. 2018; 821 9 Zeng MT, Xu W, Liu X, Chang CZ, Zhu H, Dong ZB. Eur. J. Org. Chem. 2017; 6060 10a Wu YX, Peng K, Li JH, Dong ZB. Synthesis 2020; 52: 3001 10b Wang X, Wu CY, Li YS, Dong ZB. Eur. J. Org. Chem. 2020; 6770 11a Liu X, Dong ZB. J. Org. Chem. 2019; 84: 11524 11b Dong ZB, Balkenhohl M, Tan E, Knochel P. Org. Lett. 2018; 20: 7581 11c Zhang SB, Liu X, Gao MY, Dong ZB. J. Org. Chem. 2018; 83: 14933 11d Chang CZ, Liu X, Zhu H, Dong ZB. J. Org. Chem. 2018; 83: 13530 11e Liu X, Zhang SB, Zhu H, Dong ZB. J. Org. Chem. 2018; 83: 11703 11f Liu X, Liu M, Xu W, Zeng MT, Zhu H, Chang CZ, Dong ZB. Green Chem. 2017; 19: 5591 12a Zeng MT, Wang M, Peng HY, Cheng Y, Dong ZB. Synthesis 2018; 50: 644 12b Peng HY, Wu YX, Dong ZB. Synthesis 2020; 52: 135 12c Liu Y, Bao W. Tetrahedron Lett. 2007; 48: 4785 13 CCDC 2100854 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures Supplementary Material Supplementary Material Supporting Information