An Efficient Copper-Catalyzed C(sp²)–S Formation Starting from Aryl Iodides and Tetramethylthiuram Monosulfide (TMTM)

Abstract

A new, efficient copper-catalyzed C(sp²)–S formation of phenyl dithiocarbamates starting from aryl iodides and tetramethylthiuram monosulfide (TMTM) was developed. The target compounds, phenyl dithiocarbamates with active sites, were synthesized smoothly in good to excellent yields. The easy performance, high yields, decent functional group compatibility, and cost-effective substrates make the protocol practical and attractive in C–S bond formation.

Key words

aryl iodide - thiuram - sulfur - bond formation - dithiocarbamates

• References

• 1a Zeng M.-T, Xu W, Liu M, Liu X, Chang C.-Z, Zhu H, Dong Z.-B. Synth. Commun. 2017; 47: 1434
• 1b Zeng M.-T, Xu W, Liu X, Chang C.-Z, Zhu H, Dong Z.-B. Eur. J. Org. Chem. 2017; 6060
• 1c Wu X.-M, Yan G.-B. Synlett 2019; 30: 610
• 2 Enders D, Rembiak A, Liebich JX. Synthesis 2011; 281
• 3a Doyon G, Zerbato J, Mellors JW, Sluis-Cremer N. AIDS 2013; 27: F7
• 3b Nash T, Rice WG. Antimicrob. Agents Chemother. 1998; 42: 1488
• 3c Bouma MJ, Snowdon D, Fairlamb AH, Ackers JP. Antimicrob. Agents Chemother. 1998; 42: 817
• 4 Len C, Postel D, Ronco G, Villa P. Agric. Food Chem. 1997; 45: 3
• 5 Fujii S, Yoshimura T. Coord. Chem. Rev. 2000; 198: 89
• 6a D’hooghe M, De Kimpe N. Tetrahedron 2006; 62: 513
• 6b Erian AW, Sherif SM. Tetrahedron 1999; 55: 7957
• 6c Goel A, Mazur SJ, Fattah RJ, Hartman TL, Turpin JA, Huang M, Rice WG, Appella E, Inman JK. Bioorg. Med. Chem. Lett. 2002; 12: 767
• 6d Nagano R, Shibata K, Naito T, Fuse A, Asano K, Hashizume T, Nakagawa S. Antimicrob. Agents Chemother. 1997; 41: 2278
• 6e Urlyapova NG, Yushchenko AA, Daudova AD, Makarov VA. Bull. Exp. Biol. Med. 2006; 143: 327
• 7 Rafin C, Veignie E, Sancholle M, Postel D, Len C, Villa P, Ronco GJ. Agric. Food Chem. 2000; 48: 5283
• 8a Boas U, Gertz H, Christensen JB, Heegaard PM. Tetrahedron Lett. 2004; 45: 269
• 8b Mukerjee AK, Ashare R. Chem. Rev. 1991; 91: 1
• 8c Liu Y, Bao W. Tetrahedron Lett. 2007; 48: 4785
• 9a Bakkestuen AK, Gundersen LL. Tetrahedron Lett. 2003; 44: 3359
• 9b Kotali E, Varvoglis A. J. Chem. Soc., Perkin Trans. 1 1987; 2759
• 9c Sondhi M, Verma RP, Singhal N, Shukla R, Raghubir R, Dubey MP. Indian Drugs 1999; 36: 50
• 10 Peng K, Zhu H, Liu X, Peng H.-Y, Chen J.-Q, Dong Z.-B. Eur. J. Org. Chem. 2019; 7629
• 11a Jen K, Cava MP. Tetrahedron Lett. 1982; 23: 2001
• 11b Krasovskiy A, Gavryushin A, Knochel P. Synlett 2005; 2691
• 11c Krasovskiy A, Gavryushin A, Knochel P. Synlett 2006; 792
• 11d Grunwell JR. J. Org. Chem. 1970; 35: 1500
• 11e Krasovskiy A, Malakhov V, Gavryushin A, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040
• 11f Gronowitz S, Hornfeldt AB, Temciuc M. Synthesis 1993; 483
• 12a Azizi N, Aryanasab F, Saidi MR. Org. Lett. 2006; 8: 5275
• 12b Bhadra S, Saha A, Ranu BC. Green Chem. 2008; 10: 1224
• 13 Xu W, Gao F, Dong Z.-B. Eur. J. Org. Chem. 2018; 821
• 14a Dong Z.-B, Liu X, Bolm C. Org. Lett. 2017; 19: 5916
• 14b Cao Q, Peng H.-Y, Cheng Y, Dong Z.-B. Synthesis 2018; 50: 1527
• 15a Liu X, Dong Z.-B. J. Org. Chem. 2019; 84: 11524
• 15b Dong Z.-B, Balkenhohl M, Tan E, Knochel P. Org. Lett. 2018; 20: 7581
• 15c Zhang S.-B, Liu X, Gao M.-Y, Dong Z.-B. J. Org. Chem. 2018; 83: 14933
• 15d Chang C.-Z, Liu X, Zhu H, Dong Z.-B. J. Org. Chem. 2018; 83: 13530
• 15e Liu X, Zhang S.-B, Zhu H, Dong Z.-B. J. Org. Chem. 2018; 83: 11703
• 15f Liu X, Liu M, Xu W, Zeng M.-T, Zhu H, Chang C.-Z, Dong Z.-B. Green Chem. 2017; 19: 5591
• 15g Liu X, Cao Q, Xu W, Zeng M.-T, Dong Z.-B. Eur. J. Org. Chem. 2017; 5795
• 15h Cheng Y, Liu X, Dong Z.-B. Eur. J. Org. Chem. 2018; 815
• 15i Liu X, Zhang S.-B, Zhu H, Cheng Y, Peng H.-Y, Dong Z.-B. Eur. J. Org. Chem. 2018; 4483
• 15j Gao M.-Y, Xu W, Zhang S.-B, Li Y.-S, Dong Z.-B. Eur. J. Org. Chem. 2018; 6693
• 15k Zhu H, Zhang S.-B, Liu X, Chen Y, Peng H.-Y, Dong Z.-B. Eur. J. Org. Chem. 2018; 5711
• 16a Zeng M.-T, Wang M, Peng H.-Y, Cheng Y, Dong Z.-B. Synthesis 2018; 50: 644
• 16b Peng H.-Y, Wu Y.-X, Dong Z.-B. Synthesis 2020; 52: 135