A Regioselective and Convergent Paired Electrochemical Synthesis of N,N′-Diphenyl-3-sulfonyl-[1,1′-biphenyl]-4,4′-diamines

Abstract

A regioselective synthesis of N,N′-diphenyl-3-sulfonyl-[1,1′-biphenyl]-4,4′-diamine derivatives is carried out by anodic oxidation of N,N′-diphenylbenzidine in the presence of sulfinic acids as nucleophiles via a convergent paired electrochemical process. The sulfonylated aromatic amine products are obtained under mild reaction conditions with high yields, high current efficiency and atom economy.

Key words

regioselective synthesis - electrosynthesis - Michael acceptors - cyclic voltammetry - convergent paired synthesis - N,N′-diphenylbenzidine

• References

• 1 Lawrence SA. Amines: Synthesis Properties and Applications . Cambridge University Press; Cambridge: 2004
• 2 Kenny JR, Maggs JL, Meng X, Sinnott D, Clarke SE, Park BK, Stachulski AV. J. Med. Chem. 2004; 47: 2816
• 3 Zhang L, Wang W, Fan R. Org. Lett. 2013; 15: 2018
• 4 Ricci A. Amino Group Chemistry: From Synthesis to the Life Sciences. Wiley-VCH; Weinheim: 2008
• 5 Riess W, Riel H, Beierlein T, Brutting W, Muller P, Seidler PF. IBM J. Res. Dev. 2001; 45: 77
• 6 Alexy M, Hanko M, Rentmeister S, Heinze J. Sens. Actuators, B 2006; 114: 916
• 7 Yurchenko O, Freytag D, zur Borg L, Zentel R, Heinze J, Ludwigs S. J. Phys. Chem. B 2012; 116: 30
• 8 Matis M, Rapta P, Lukeš V, Hartmann H, Dunsch L. J. Phys. Chem. B 2010; 114: 4451
• 9 Bondarchuk SV, Minaev BF. J. Phys. Org. Chem. 2014; 27: 640
• 10 Chen J, Ma D. Appl. Phys. Lett. 2005; 87: 023505
• 11 Macías-Ruvalcaba NA, Evans DH. J. Phys. Chem. C 2007; 111: 5805
• 12 Tan NC, van Leeuwen A, van Voorthuizen EM, Slenders P, Prenafeta-Boldu FX, Temmink H, Lettinga G, Field JA. Biodegradation 2005; 16: 527
• 13 Otzen T, Wempe EG, Kunz B, Bartels R, Lehwark-Yvetot G, Hansel W, Schaper KJ, Seydel JK. J. Med. Chem. 2004; 47: 240
• 14 Zhu W, Ma D. J. Org. Chem. 2005; 70: 2696
• 15 Kantam ML, Neelima B, Sreedhar B, Chakravarti R. Synlett 2008; 1455
• 16 Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W, Ethier D, Evans JF, Ford-Hutchison AW, Gauthier JY, Gordon R, Guay J, Gresser M, Kargman S, Kennedy B, Leblanc Y, Leger S, Mancini J, O’Neill GP, Ouellet M, Percival MD, Perrier H, Riendeau D, Rodger I, Tagari P, Therien M, Vickers P, Wong E, Xu LJ, Young RN, Zamboni R. Bioorg. Med. Chem. Lett. 1999; 9: 1773
• 17 Hu W, Guo Z, Chu F, Bai A, Yi X, Cheng G, Li J. Bioorg. Med. Chem. Lett. 2003; 13: 1153
• 18 Nematollahi D, Hosseiny-Davarani SS, Mirahmadpour P. ACS Sustainable Chem. Eng. 2014; 2: 579
• 19 Steckhan E, Arns T, Heineman WR, Hilt G, Hoormann D, Jorissen J, Kroner L, Lewall B, Putter H. Chemosphere 2001; 43: 63
• 20 Ibanez JG, Fitch A, Frontana-Uribe BA, Vasquez-Medrano R. Green Electrochemistry . In Encyclopedia of Applied Electrochemistry . Springer-Verlag; New York: 2014
• 21 Sharafi-Kolkeshvandi M, Nematollahi D, Nikpour F, Dadpou B, Alizadeh H. Electrochim. Acta 2016; 214: 147
• 22 Sharafi-Kolkeshvandi M, Nematollahi D, Nikpour F, Salahifar E. New J. Chem. 2016; 40: 5442
• 23 Khazalpour S, Nematollahi D. Green Chem. 2015; 17: 3508
• 24 Salahifar E, Nematollahi D, Bayat M, Mahyari A, Amiri-Rudbari H. Org. Lett. 2015; 17: 4666
• 25 Sharafi-Kolkeshvandi M, Nematollahi D, Nikpour F. J. Electrochem. Soc. 2016; 163: G75
• 26 Niu J, Lee JY, Neudeck A, Dunsch L. Synth. Met. 1999; 99: 133
• 27 Kim Y, Kijong H. Macromolecules 2002; 35: 8759
• 28 Yang H, Bard AJ. J. Electroanal. Chem. 1991; 306: 87
• 29 Debrodt H, Heusler KE. Electrochim. Acta 1982; 27: 189
• 30 Sarver LA, Kolthoff IM. J. Am. Chem. Soc. 1937; 59: 23
• 31 Trost BM. Science 1991; 254: 1471
• 32 Cann MC, Connelly ME. Real-World Cases in Green Chemistry . American Chemical Society; Washington DC: 2000