1,1-Difunctionalization of α‑Carbonyl Sulfur Ylides with Thiosulfonates: Synthesis of β-Keto Thiosulfones

Abstract

1,1-Difunctionalization of α‑carbonyl sulfur ylides and thiosulfonates under simple conditions is disclosed. In this protocol, two new C–S bonds are constructed in a one-step reaction. A series of aliphatic and aromatic β-keto thiosulfones were obtained in moderate to good yields. This reaction probably proceeds through sulfur ylide-involved­ nucleophilic substitution of an ion pair within a solvent cage.

Key words

1,1-difunctionalization - sulfur ylides - thiosulfonates - β-keto thiosulfones - organosulfur chemistry

Publication History

Received: 11 February 2022

Accepted after revision: 30 March 2022

Accepted Manuscript online:
30 March 2022

Article published online:
10 May 2022

• References

• 1a Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1965; 87: 1353
• 1b Johnson AW, LaCount RB. J. Am. Chem. Soc. 1961; 83: 417
• 2a Akagawa K, Takigawa S, Nagamine IS, Umezawa R, Kudo K. Org. Lett. 2013; 15. 4964
• 2b Yuan Z, Fang X, Li X, Wu J, Yao H, Lin A. J. Org. Chem. 2015; 80: 11123
• 2c Oswald MF, Raw SA, Taylor RJ. Chem. Commun. 2005; 2253
• 2d Shao J, Chen W, Zhao M, Shu K, Liu H, Tang P. Org. Lett. 2018; 20: 3992
• 2e Kunz RK, MacMillan DW. J. Am. Chem. Soc. 2005; 127: 3240
• 2f Oswald MF, Raw SA, Taylor RJ. Org. Lett. 2004; 6: 3997
• 3a Aggarwal VK, Hynd G, Picoul W, Vasse JL. J. Am. Chem. Soc. 2002; 124: 9964
• 3b Aggarwal VK, Charmant JP. H, Fuentes D, Harvey JN, Hynd G, Ohara D, Picoul W, Robiette R, Smith C, Vasse J, Winn CL. J. Am. Chem. Soc. 2006; 128: 2105
• 3c Illa O, Arshad M, Ros A, McGarrigle EM, Aggarwal VK. J. Am. Chem. Soc. 2010; 132: 1828
• 3d Boratynski PJ, Skarzewski J. J. Org. Chem. 2013; 78: 4473
• 3e Wu HY, Chang CW, Chein RJ. J. Org. Chem. 2013; 78: 5788
• 4a Chen XM, Xie KX, Yue DF, Zhang XM, Xu XY, Yuan WC. Tetrahedron 2018; 74: 600
• 4b Lei X, Jiang CH, Wen X, Xu QL, Sun H. RSC. Adv. 2015; 5: 14953
• 4c Shao J, Chen W, Ying Z, Liu S, Luo F, Ou L. Org. Lett. 2019; 21: 6370
• 4d Jha BK, Prudhviraj J, Mainkar PS, Punna N, Chandrasekhar S. RSC. Adv. 2020; 10: 38588
• 5a Zhu BH, Zheng JC, Yu CB, Sun XL, Zhou YG, Shen Q, Tang Y. Org. Lett. 2010; 12: 504
• 5b Morton D, Pearson D, Field RA, Stockman RA. Chem. Commun. 2006; 1833
• 5c Aggarwal VK, Vasse JL. Org. Lett. 2003; 5: 3987
• 6a Lu LQ, Cao YJ, Liu XP, An J, Yao CJ, Ming ZH, Xiao WJ. J. Am. Chem. Soc. 2008; 130: 6946
• 6b Lu LQ, Li F, An J, Cheng Y, Chen JR, Xiao WJ. Chem. Eur. J. 2012; 18: 4073
• 7a Punna N, Das P, Gouverneur V, Shibata N. Org. Lett. 2018; 20: 1526
• 7b Liu YY, Yu XY, Chen JR, Qiao MM, Qi X, Shi DQ, Xiao WJ. Angew. Chem. Int. Ed. 2017; 56: 9527
• 7c Wang Q, Qi X, Lu LQ, Li TR, Yuan ZG, Zhang K, Li BJ, Lan Y, Xiao WJ. Angew. Chem. Int. Ed. 2016; 55: 2840
• 8a Yang L, Zhou S, Zhao JQ, You Y, Wang ZH, Zhou MQ, Yuan WC. Org. Biomol. Chem. 2021; 19: 3678
• 8b He Y, Lou J, Zhou YG, Yu Z. Chem. Eur. J. 2020; 26: 4941
• 9a Lu LQ, Zhang JJ, Li F, Cheng Y, An J, Chen JR, Xiao WJ. Angew. Chem. Int. Ed. 2010; 49: 4495
• 9b Chen JR, Dong WR, Candy M, Pan FF, Jorres M, Bolm C. J. Am. Chem. Soc. 2012; 134: 6924
• 9c Guo W, Luo Y, Sung HH. Y, Williams ID, Li P, Sun J. J. Am. Chem. Soc. 2020;  142: 14384
• 9d Caiuby CA, Furniel LG, Burtoloso AC. Chem. Sci. 2022; 13: 1192
• 9e Kaiser D, Klose I, Oost R, Neuhaus J, Maulide N. Chem. Rev. 2019; 119: 8701
• 10a Wang N, Jia Y, Qin H, Jiang ZX, Yang Z. Org. Lett. 2020; 22: 7378
• 10b Qin H, Jia Y, Wang N, Jiang ZX, Yang Z. Chem. Commun. 2020; 56: 8265
• 11a Pluta K, Morak-Młodawska B, Jeleń M. Eur. J. Med. Chem. 2011; 46: 3179
• 11b Mellah M, Voituriez A, Schulz E. Chem. Rev. 2007; 107: 5133
• 11c Wang D, Cao P, Wang B, Jia T, Lou Y, Wang M, Liao J. Org. Lett. 2015; 17: 2420
• 11d Bhargav A, Ma Y, Shashikala K, Cui Y, Losovyj Y, Fu Y. J. Mater. Chem. A 2017; 5: 25005
• 12a Harrak Y, Casula G, Basset J, Rosell G, Plescia S, Raffa D, Cusimano MG, Pouplana R, Pujol MD. J. Med. Chem. 2010; 53: 6560
• 12b Sasikumar TK, Qiang L, Burnett DA, Cole D, Xu R, Li H, Greenlee WJ, Clader J, Zhang L, Hyde L. Bioorg. Med. Chem. Lett. 2010; 20: 3632
• 13 Churcher I, Beher D, Best JD, Castro JL, Clarke EE, Gentry A, Harrison T, Hitzel L, Kay E, Kerrad S, Lewis HD, Morentin-Gutierrez P, Mortishire-Smith R, Oakley PJ, Reilly M, Shaw DE, Shearman MS, Teall MR, Williams S, Wrigley JD. Bioorg. Med. Chem. Lett. 2006; 16: 280
• 14a Cornes D. Patent WO 2002/100173, 2002
• 14b Wichert RA, Beckett TH. Patent WO 2002/019823, 2002
• 15a Xiang J, Ipek M, Suri V, Tam M, Xing Y, Huang N, Zhang Y, Tobin J, Mansour TS, McKew J. Bioorg. Med. Chem. 2007; 15: 4396
• 15b Xiang J, Ipek M, Suri V, Massefski W, Pan N, Ge Y, Tam M, Xing Y, Tobin JF, Xu X, Tam S. Bioorg. Med. Chem. Lett. 2005; 15: 2865
• 15c Curti C, Laget M, Carle AO, Gellis A, Vanelle P. Eur. J. Med. Chem. 2007; 42: 880
• 15d Reddy RJ, Kumari AH, Kumar JJ. Org. Biomol. Chem. 2021; 19: 3087
• 16a Fang Y, Rogge T, Ackermann L, Wang SY, Ji SJ. Nat. Commun. 2018; 9: 1
• 16b Li J, Rao WD, Wang SY, Ji SJ. J. Org. Chem. 2019; 84: 11542
• 16c Kanemoto K, Yoshida S, Hosoya T. Org. Lett. 2019; 21: 3172
• 16d Rao CQ, Mai SY, Song QL. Chem. Commun. 2018; 54: 5964
• 16e Mampuys P, Zhu Y.-P, Sergeyev S, Ruijter E, Orru RV. A, Van Doorslaer S, Maes BU. W. Org. Lett. 2016; 18: 2808
• 16f Peng ZY, Yin HL, Zhang H, Jia TZ. Org. Lett. 2020; 22: 5885
• 16g Mampuys P, McElroy CR, Clark JH, Orru RV. A, Maes BU. W. Adv. Synth. Catal. 2020; 362: 3
• 17 Yuan H, Nuligonda T, Gao H, Tung CH, Xu Z. Org. Chem. Front. 2018; 5: 1371
• 18 Huang S, Thirupathi N, Tung CH, Xu Z. J. Org. Chem. 2018; 83: 9449
• 19 Wang F, Liu BX, Rao W, Wang SY. Org. Lett. 2020; 22: 6600
• 20a Jiang W, Li N, Zhou L, Zeng Q. ACS. Catal. 2018; 8: 9899
• 20b Chen H, Chen L, He Z, Zeng Q. Green Chem. 2021; 23: 2624
• 20c Xu C, He Z, Kang X, Zeng Q. Green Chem. 2021; 23: 7544
• 20d Zhang Q, Feng H, Chen F, He Z, Zeng Q. J. Org. Chem. 2021; 86: 7806
• 21a Huang Y, Li J, Chen H, He Z, Zeng Q. Chem. Rec. 2021; 21: 1216
• 21b Zheng W, Tan M, Yang L, Zhou L, Zeng Q. Eur. J. Org. Chem. 2020; 11: 1764
• 22 Kang X, Liang X, Zeng Q. Org. Lett. 2021; 23: 7477
• 23 Fujiki K, Tanifuji N, Sasaki Y, Yokoyama T. Synthesis 2002; 343
• 24 Xiao Z, Wang L, Wei J, Ran C, Liang SH, Shang J, Zheng C. Chem. Commun. 2020; 56: 4164
• 25a Ratts KW, Yao AN. J. Org. Chem. 1966; 31: 1185
• 25b Payne G. J. Org. Chem. 1967; 32: 3351
• 25c Ushakov PY, Khatuntseva EA, Nelyubina YV, Tabolin AA, Ioffe SL, Sukhorukov AY. Adv. Synth. Catal. 2019; 361: 5322