Efficient α-Arylation of α-Fluoro-α-nitrosulfonylmethanes Employing Diaryliodonium Salts

Abstract

Reported herein is an efficient α-arylation of α-fluoro-α-nitro­sulfonylmethanes using diaryliodonium salts. A wide range of α-fluoronitrosulfonylmethane substrates underwent α-arylation smoothly to produce the corresponding adducts bearing a fully substituted fluorocarbon center in good to excellent yields. The protocol was subsequently shown viable for the α-arylation of α-cyano-α-fluorosulfonylmethane derivatives yielding highly valuable cyano building blocks.

Key words

α-fluoro-α-nitrosulfonylmethanes - diaryliodonium salts - α-arylation - α-fluoro(phenylsulfonyl)acetonitriles - metal-free

Publication History

Received: 28 June 2022

Accepted after revision: 12 June 2023

Accepted Manuscript online:
12 June 2023

Article published online:
17 July 2023

• References

• 1a Konduru NK, Dey S, Sajid M, Owais M, Ahmed N. Eur. J. Med. Chem. 2013; 59: 23
• 1b El-Awa A, Noshi MN, du Jourdin XM, Fuchs PL. Chem. Rev. 2009; 109: 2315
• 1c Curti C, Laget M, Carle AO, Gellis A, Vanelle P. Eur. J. Med. Chem. 2007; 42: 880
• 1d Billard W, Binch H, Bratzler K, Chen L.-Y, Crosby GJr, Duffy RA, Dugar S, Lachowicz J, McQuade R, Pushpavanam P, Ruperto VB, Taylor LA, Clader JW. Bioorg. Med. Chem. Lett. 2000; 10: 2209
• 1e Simpkins NS. Sulphones in Organic Synthesis, Tetrahedron Organic Chemistry Series, Vol. 10. Baldwin JE, Magnus PD. Pergamon; Oxford: 1993
• 2a Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 2668
• 2b Nielsen M, Jacobsen CB, Paixão MW, Holub N, Jørgensen KA. J. Am. Chem. Soc. 2009; 131: 10581
• 3 Nájera C, Yus M. Tetrahedron 1999; 55: 10547
• 4 Prakash GK. S, Hu J. Acc. Chem. Res. 2007; 40: 921
• 5a Shen X, Hu J. Eur. J. Org. Chem. 2014; 4437
• 5b Shen X, Miao W, Ni C, Hu J. Angew. Chem. Int. Ed. 2014; 53: 775
• 5c Shen X, Zhang W, Zhang L, Luo T, Wan X, Gu Y, Hu J. Angew. Chem. Int. Ed. 2012; 51: 6966
• 5d Zhang W, Hu J. Adv. Synth. Catal. 2010; 352: 2799
• 5e Prakash GK. S, Chacko S, Vaghoo H, Shao N, Gurung L, Mathew T, Olah GA. Org. Lett. 2009; 11: 1127
• 5f Furukawa T, Shibata N, Mizuta S, Nakamura S, Toru T, Shiro M. Angew. Chem. Int. Ed. 2008; 47: 8051
• 5g Prakash GK. S, Ledneczki I, Chacko S, Olah GA. Org. Lett. 2008; 10: 557
• 5h Fukuzumi T, Shibata N, Sugiura M, Yasui H, Nakamura S, Toru T. Angew. Chem. Int. Ed. 2006; 45: 4973
• 5i Ni C, Li Y, Hu J. J. Org. Chem. 2006; 71: 6829
• 5j Beare NA, Hartwig JF. J. Org. Chem. 2002; 67: 541
• 6a Ni C, Hu M, Hu J. Chem. Rev. 2015; 115: 765
• 6b Ge S, Chaładaj W, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 4149
• 6c Jiang X.-L, Chen Z.-H, Xu X.-H, Qing F.-L. Org. Chem. Front. 2014; 1: 774
• 6d Mizuta S, Stenhagen IS. R, O’Duill M, Wolstenhulme J, Kirjavainen AK, Forsback SJ, Tredwell M, Sandford G, Moore PR, Huiban M, Luthra SK, Passchier J, Solin O, Gouverneur V. Org. Lett. 2013; 15: 2648
• 6e Xia J.-B, Zhu C, Chen C. J. Am. Chem. Soc. 2013; 135: 17494
• 6f Fujiwara Y, Dixon JA, Rodriguez RA, Baxter RD, Dixon DD, Collins MR, Blackmond DG, Baran PS. J. Am. Chem. Soc. 2012; 134: 1494
• 6g Fier PS, Hartwig JF. J. Am. Chem. Soc. 2012; 134: 5524
• 6h Prakash GK. S, Ganesh SK, Jones J.-P, Kulkarni A, Masood K, Swabeck JK, Olah GA. Angew. Chem. Int. Ed. 2012; 51: 12090
• 6i Fujikawa K, Fujioka Y, Kobayashi A, Amii H. Org. Lett. 2011; 13: 5560
• 7a Feng Z, Min Q.-Q, Fu X.-P, An L, Zhang X. Nat. Chem. 2017; 9: 918
• 7b Charpentier J, Früh N, Togni A. Chem. Rev. 2015; 115: 650
• 7c Liang T, Neumann CN, Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
• 7d Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455
• 7e Hu J, Zhang W, Wang F. Chem. Commun. 2009; 7465
• 7f Mikami K, Itoh Y, Yamanaka M. Chem. Rev. 2004; 104: 1
• 8a Zhao Y, Ni C, Jiang F, Gao B, Shen X, Hu J. ACS Catal. 2013; 3: 631
• 8b Zhao Y, Gao B, Ni C, Hu J. Org. Lett. 2012; 14: 6080
• 8c Ni C, Hu J. Synlett 2011; 770
• 9 Su Y.-M, Feng G.-S, Wang Z.-Y, Lan Q, Wang X.-S. Angew. Chem. Int. Ed. 2015; 54: 6003

For selected reviews, see:
• 10a Hyatt IF. D, Dave L, David N, Kaur K, Medard M, Mowdawalla C. Org. Biomol. Chem. 2019; 17: 7822
• 10b Fañanás-Mastral M. Synthesis 2017; 49: 1905
• 10c Aradi K, Tóth BL, Tolnai GL, Novák Z. Synlett 2016; 27: 1456
• 11a An Y, Zhang X.-M, Li Z.-Y, Xiong W.-H, Yu R.-D, Zhang F.-M. Chem. Commun. 2019; 55: 119
• 11b Mao S, Geng X, Yang Y, Qian X, Wu S, Han J, Wang L. RSC Adv. 2015; 5: 36390
• 11c Dey C, Lindstedt E, Olofsson B. Org. Lett. 2015; 17: 4554
• 11d Monastyrskyi A, Namelikonda NK, Manetsch R. J. Org. Chem. 2015; 80: 2513
• 11e Chai Z, Wang B, Chen J.-N, Yang G. Adv. Synth. Catal. 2014; 356: 2714
• 11f Oh CH, Kim JS, Jung HH. J. Org. Chem. 1999; 64: 1338
• 11g Chen K, Koser GF. J. Org. Chem. 1991; 56: 5764
• 12a Zaheer MK, Gupta E, Kant R, Mohanan K. Chem. Commun. 2020; 56: 153
• 12b Zaheer MK, Vaishanv NK, Kant R, Mohanan K. Chem. Asian J. 2020; 15: 4297
• 13a Stuart DR. Chem. Eur. J. 2017; 23: 15852
• 13b Yusubov MS, Maskaev AV, Zhdankin VV. ARKIVOC 2011; (i): 370
• 13c Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
• 14 CCDC 2211666 (3w) 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
• 15 Arseniyadis S, Kyler KS, Watt DS. Org. React. 1984; 31: 1
• 16a Malmgren J, Santoro S, Jalalian N, Himo F, Olofsson B. Chem. Eur. J. 2013; 19: 10334
• 16b Norrby P.-O, Petersen TB, Bielawski M, Olofsson B. Chem. Eur. J. 2010; 16: 8251
• 17a Weigl U, Heimberger M, Pierik AJ, Rétey J. Chem. Eur. J. 2003; 9: 652
• 17b Prakash GK. S, Wang F, Zhang Z, Ni C, Haiges R, Olah GA. Org. Lett. 2012; 14: 3260
• 18 Tsui GC, Glenadel Q, Lau C, Lautens M. Org. Lett. 2011; 13: 208
• 19 Sundalam SK, Nilova A, Seidl TL, Stuart DR. Angew. Chem. Int. Ed. 2016; 55: 8431