Recent Developments on the Synthesis of Sulfoxides via Sulfenate Anions

Abstract

Since the early 2000s, novel synthetic methods for the preparation of sulfoxides have emerged that involve sulfenate anions as sulfur nucleophiles. This short review showcases key advances in these sulfenate protocols, including catalytic enantioselective alkylation and arylation, and provides future directions for this research field.

1 Introduction

2 Precursors of Sulfenate Anions

3 Organocatalytic Enantioselective Alkylation of Sulfenate Anions

4 Palladium-Catalyzed Arylation of Sulfenate Anions

5 Coupling of Sulfenate Anions with Hypervalent Iodine Reagents

6 Conclusions and Outlook

Key words

sulfoxides - sulfenate anions - organocatalysis - palladium - hypervalent iodine reagents

Publication History

Received: 18 July 2023

Accepted after revision: 16 August 2023

Accepted Manuscript online:
16 August 2023

Article published online:
27 September 2023

• References

• 1 Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5
• 2a Jia T, Cao P, Wang B, Lou Y, Yin X, Wang M, Liao J. J. Am. Chem. Soc. 2015; 137: 13760
• 2b Yuan C.-H, Wang X.-X, Jiao L. Angew. Chem. Int. Ed. 2023; 62: e202300854
• 3a Kosugi H, Konta H, Uda H. J. Chem. Soc., Chem. Commun. 1985; 211
• 3b Solladié G, Demailly G, Greck C. Tetrahedron Lett. 1985; 26: 435
• 4a Pitchen P, Dunach E, Deshmukh MN, Kagan HB. J. Am. Chem. Soc. 1984; 106: 8188
• 4b Di Furia F, Modena G, Seraglia R. Synthesis 1984; 325
• 5 Egami H, Katsuki T. J. Am. Chem. Soc. 2007; 129: 8940
• 6a Andersen KK. Tetrahedron Lett. 1962; 3: 93
• 6b Andersen KK, Gaffield W, Papanikolaou NE, Foley JW, Perkins RI. J. Am. Chem. Soc. 1964; 86: 5637
• 7a Furukawa N, Konno Y, Tsuruoka M, Ogawa S. Heteroat. Chem. 1992; 3: 495
• 7b Refvik MD, Froese RD. J, Goddard JD, Pham HH, Pippert MF, Schwan AL. J. Am. Chem. Soc. 1995; 117: 184
• 7c Sandrinelli F, Perrio S, Beslin P. J. Org. Chem. 1997; 62: 8626
• 8 Riddell AB, Smith MR. A, Schwan AL. J. Sulfur Chem. 2022; 43: 540
• 9 Maitro G, Prestat G, Madec D, Poli G. Tetrahedron: Asymmetry 2010; 21: 1075
• 10 Yang L, Wang B, Yin X, Zeng Q. Chem. Rec. 2022; 22: e202100242
• 11a Zhang M, Jia T, Yin H, Carroll PJ, Schelter EJ, Walsh PJ. Angew. Chem. Int. Ed. 2014; 53: 10755
• 11b Zhang M, Jia T, Wang CY, Walsh PJ. J. Am. Chem. Soc. 2015; 137: 10346
• 11c Li M, Berritt S, Wang C, Yang X, Liu Y, Sha S.-C, Wang B, Wang R, Gao X, Li Z, Fan X, Tao Y, Walsh PJ. Nat. Commun. 2018; 9: 1754
• 11d Zheng Z, Pu Y, Adrio J, Walsh PJ. Angew. Chem. Int. Ed. 2023; 62: e202303069
• 12 Gelat F, Lohier JF, Gaumont AC, Perrio S. Adv. Synth. Catal. 2015; 357: 2011
• 13 Caupène C, Boudou C, Perrio S, Metzner P. J. Org. Chem. 2005; 70: 2812
• 14 Foucoin F, Caupène C, Lohier J.-F, Sopkova de Oliveira Santos J, Perrio S, Metzner P. Synthesis 2007; 1315
• 15 O’Donnell JS, Schwan AL. Tetrahedron Lett. 2003; 44: 6293
• 16 Gelat F, Jayashankaran J, Lohier J.-F, Gaumont A.-C, Perrio S. Org. Lett. 2011; 13: 3170
• 17 Bernoud E, Le Duc G, Bantreil X, Prestat G, Madec D, Poli G. Org. Lett. 2010; 12: 320
• 18 Izquierdo F, Chartoire A, Nolan SP. ACS Catal. 2013; 3: 2190
• 19 Jia T, Bellomo A, Montel S, Zhang M, El Baina K, Zheng B, Walsh PJ. Angew. Chem. Int. Ed. 2014; 53: 260
• 20 Zhang M, Jia T, Sagamanova IK, Pericás MA, Walsh PJ. Org. Lett. 2015; 17: 1164
• 21 Chang M.-Y, Cheng Y.-C, Chan C.-K. Tetrahedron 2016; 72: 4068
• 22 Gelat F, Gaumont A.-C, Perrio S. J. Sulfur Chem. 2013; 34: 596
• 23 Zong L, Ban X, Kee CW, Tan C.-H. Angew. Chem. Int. Ed. 2014; 53: 11849
• 24 Maitro G, Prestat G, Madec D, Poli G. J. Org. Chem. 2006; 71: 7449
• 25 Maitro G, Vogel S, Prestat G, Madec D, Poli G. Org. Lett. 2006; 8: 5951
• 26 Colobert F, Ballesteros-Garrido R, Leroux FR, Ballesteros R, Abarca B. Tetrahedron Lett. 2007; 48: 6896
• 27 Maitro G, Vogel S, Sadaoui M, Prestat G, Madec D, Poli G. Org. Lett. 2007; 9: 5493
• 28 Jia T, Zhang M, McCollom SP, Bellomo A, Montel S, Mao J, Dreher SD, Welch CJ, Regalado EL, Williamson RT, Manor BC, Tomson NC, Walsh PJ. J. Am. Chem. Soc. 2017; 139: 8337
• 29 Jia T, Zhang M, Jiang H, Wang CY, Walsh PJ. J. Am. Chem. Soc. 2015; 137: 13887
• 30 Jiang H, Jia T, Zhang M, Walsh PJ. Org. Lett. 2016; 18: 972
• 31 Wu C, Berritt S, Liang X, Walsh PJ. Org. Lett. 2019; 21: 960
• 32 Wang L, Chen M, Zhang P, Li W, Zhang J. J. Am. Chem. Soc. 2018; 140: 3467
• 33 Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
• 34a Frei R, Wodrich MD, Hari DP, Borin P.-A, Chauvier C, Waser J. J. Am. Chem. Soc. 2014; 136: 16563
• 34b Castoldi L, Di Tommaso EM, Reitti M, Gräfen B, Olofsson B. Angew. Chem. Int. Ed. 2020; 59: 15512
• 34c Sarkar S, Wojciechowska N, Rajkiewicz AA, Kalek M. Eur. J. Org. Chem. 2022; e202101408
• 35a Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
• 35b Umierski N, Manolikakes G. Org. Lett. 2013; 15: 4972
• 35c Chen CC, Waser J. Org. Lett. 2015; 17: 736
• 36 Yu H, Li Z, Bolm C. Org. Lett. 2018; 20: 7104
• 37 Wang L, Chen M, Zhang J. Org. Chem. Front. 2019; 6: 32
• 38 Amos SG. E, Nicolai S, Gagnebin A, Le Vaillant F, Waser J. J. Org. Chem. 2019; 84: 3687
• 39 Liu B, Lim C.-H, Miyake GM. J. Am. Chem. Soc. 2017; 139: 13616
• 40 Chen L, Liang J, Chen Z.-y, Chen J, Yan M, Zhang X.-j. Adv. Synth. Catal. 2019; 361: 956
• 41 Cabrera-Afonso MJ, Granados A, Molander GA. Angew. Chem. Int. Ed. 2022; 61: e202202706
• 42 Granados A, Cabrera-Afonso MJ, Escolano M, Badir SO, Molander GA. Chem Catal. 2022; 2: 898
• 43 Saito F. Angew. Chem. Int. Ed. 2022; 61: e202213872