Synthetic Applications of Symmetrical Disulfides and Their Synthesis from Non-thiolic Substrates

Abstract

Organic disulfides are frequently found in many fields of science, ranging from chemistry to materials science to biology. While symmetrical disulfides, which have the same substitutions on the two sulfurs, are often final products, they are mostly employed as reactants and catalysts in various reactions. In addition to their usage as catalysts, their synthetic applications as reactants can arbitrarily be categorized into three types: (1) surrogates for the corresponding thiols, (2) reactants for unsymmetrical disulfides, and (3) reactants or intermediates for the other compounds. Although the straightforward, traditional way to obtain symmetrical disulfides (RSSR) is the oxidation of their parental thiols (RSH), they can also be obtained from non-thiolic compounds. This short review covers representative synthetic applications of symmetrical disulfides and their preparation methods in which the starting materials are not the corresponding thiols.

1 Introduction

2 Synthetic Applications of Symmetric Disulfides

2.1 Surrogates for Thiols

2.2 Synthesis of Unsymmetrical Disulfides

2.3 As Reactants and Intermediates

3 Synthesis of Symmetrical Disulfides from Non-thiolic Substrates

3.1 Synthesis from Organic Halides

3.2 Synthesis from Sulfonic Acid Derivatives

3.3 Synthesis from Sulfinic Acid Derivatives

3.4 Miscellaneous

4 Conclusion

Key words

symmetrical disulfide - unsymmetrical disulfide - thiol surrogate - sulfanylation - cross-coupling

Publication History

Received: 26 November 2024

Accepted after revision: 31 December 2024

Accepted Manuscript online:
31 December 2024

Article published online:
04 March 2025

• References

• 1a Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
• 1b Feng M, Tang B, Liang SH, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
• 1c Narayan M. Molecules 2020; 25: 5337
• 1d Wang Q, Guan J, Wan J, Li Z. RSC Adv. 2020; 10: 24397
• 1e Osipova V, Gracheva Y, Polovinkina M, Burmistrova D, Berberova N. Molecules 2022; 27: 3961
• 1f Lanz J, Biniaz-Harris N, Kuvaldina M, Jain S, Lewis K, Fallon BA. Antibiotics 2023; 12: 524
• 2a Kim S, Yoo H. Micromachines 2021; 12: 565
• 2b Choi K, Noh A, Kim J, Hong PH, Ko MJ, Hong SW. Polymers 2023; 15: 4408
• 2c Porter LA, Ji D, Westcott SL. Langmuir 1998; 14: 7378
• 2d Shon SL, Mazzitelly C, Murray RW. Langmuir 2001; 17: 7735
• 2e Witt D, Klajn R, Barski P, Grzybowski BA. Curr. Org. Chem. 2004; 8: 1763
• 2f Mandal B, Basu B. RSC Adv. 2014; 4: 13854
• 2g Sudharsanam R, Chandrasekaran S, Das PK. J. Mater. Chem. 2002; 12: 2904
• 3a Shimizu T, Wang H, Tanifuji N, Matsumura D, Yoshimura M, Nakanishi K, Ohta T, Yoshikawa H. Chem. Lett. 2018; 47: 678
• 3b Asenjo-Pascual J, Salmeron-Sanchez I, Avilés-Moreno JR, Mauleón P, Mazur P, Ocón P. Batteries 2022; 8: 193
• 3c Sang P, Chen Q, Wang D.-Y, Guo W, Fu Y. Chem. Rev. 2023; 123: 1262
• 4a Witt D. Synthesis 2008; 2491
• 4b Sulfur Chemistry . Jiang X. Springer Nature Switzerland; Cham: 2018
• 4c He R, Pan J, Mayer JP, Liu F. Curr. Org. Chem. 2019; 23: 2802
• 4d Ren S, Luo N, Liu K, Liu J.-B. J. Chem. Res. 2021; 45: 365
• 4e Ong CL, Khaligh NG, Juan JC. Curr. Org. Chem. 2020; 24: 550
• 4f Pramanik M, Choudhuri K, Mal P. Org. Biomol. Chem. 2020; 18: 8771
• 4g Ong CL, Titinchi S, Juan JC, Khaligh NG. Helv. Chim. Acta 2021; 104: e2100053
• 4h Jurinic CK, Belladona AL, Schumacher RF, Godoi B. Synthesis 2021; 53: 2545
• 4i Orrillo AG, Furlan RL. E. Angew. Chem. Int. Ed. 2022; 61: e202201168
• 4j Wang C, Zhang Y, Sun K, Yu T, Liu F, Wang X. Molecules 2023; 28: 1998
• 4k Wang H, Nkingwa AA, Islam F, Xu C, Zeng Q. Chem. Asian J. 2024; 19: e202300883
• 4l Sun Q, Xu Y, Yang L, Zheng C.-L, Wang G, Wang H.-B, Fang Z, Wang C.-S, Guo K. Chem. Asian J. 2024; 19: e202400124
• 5a Kondo T, Mitsudo T.-A. Chem. Rev. 2000; 100: 3205
• 5b Eichman CC, Stambuli JP. Molecules 2011; 16: 590
• 5c Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
• 5d Dong D.-Q, Hao S.-H, Yang D.-S, Wang Z.-L. Eur. J. Org. Chem. 2017; 2017: 6576
• 5e Wimmer A, König B. Beilstein J. Org. Chem. 2018; 14: 54
• 6 Patehebieke Y. Beilstein J. Org. Chem. 2020; 16: 1418
• 7a Rayner CM. Contemp. Org. Synth. 1994; 1: 191
• 7b Potkin VI, Petkevich SK, Kurman PV. Russ. J. Org. Chem. 2007; 43: 1622
• 8 Batista GM. F, de Castro PP, dos Santos JA, Skrydstrup T, Amarante GW. Org. Chem. Front. 2021; 8: 326
• 9a Watanabe Y, Numata T, Oae S. Bull. Chem. Soc. Jpn. 1982; 55: 1915
• 9b Nagase T, Akama K, Ozaki S. Chem. Lett. 1988; 17: 1385
• 9c Theobald PG, Okamura WH. J. Org. Chem. 1990; 55: 741
• 10a Khurana JM, Sahoo KP. Synth. Commun. 1992; 22: 1691
• 10b Jaisinghani HG, Khadilkar BM. Synth. Commun. 1999; 29: 3693
• 10c Soto R, Ohyama T, Kawagoe T, Baba M, Nakajo S, Kimura T, Ogawa S. Heterocycles 2001; 55: 145
• 10d Comasseto JV, Lang ES, Tercio J, Ferreira B, Simonelli F, Correia VR. J. Organomet. Chem. 1987; 334: 329
• 11a Huang D, Wu X. J. Fluorine Chem. 2021; 245: 109778
• 11b Wu D, Shiozuka A, Kawashima K, Mori T, Sekine K, Kuninobu Y. Org. Lett. 2023; 25: 3293
• 12a Szabo J, Bani-Akoto E, Dombi G, Gunther G, Bernath G, Fodor L. J. Heterocycl. Chem. 1992; 29: 1321
• 12b Repin JT, Kaltenbronn JS, Doherty AM, Hamby JM, Himmessbach RJ, Kornberg BE, Taylor MD, Lunney EA, Hamblet C, Rapundalo ST, Batley BL, Ryan MJ, Painchaud CA. J. Med. Chem. 1992; 35: 1032
• 12c Prasit P, Belley M, Evans JF, Gauthier J.-Y, Léveillé C, McFarlane CS, MacIntyre E, Peterson L, Piechuta H, Thérien M, Young RN, Zamboni R. Bioorg. Med. Chem. Lett. 1991; 1: 645
• 13a Nakagawa I, Aki K, Hata T. J. Chem. Soc., Perkin Trans. 1 1983; 1315
• 13b Beerli R, Borschberg H.-J. Helv. Chim. Acta 1992; 75: 190
• 13c Rayner CM, Sin MS, Westwell AD. Tetrahedron Lett. 1992; 33: 7237
• 13d Kanai M, Nakagawa Y, Tomioka K. Tetrahedron 1999; 55: 3831
• 14a Trost MB, Van Vranken LD. J. Am. Chem. Soc. 1991; 113: 6317
• 14b Toshimitsu A, Hirosawa C, Tanimoto S. Tetrahedron Lett. 1991; 32: 4317
• 14c Avery MA, Chong WK. M, Jennings-White C. J. Am. Chem. Soc. 1992; 114: 974
• 14d Moreno-Manas M, Arredondo Y, Pleixats R, Teixido M, Rega MM, Palacin C, Castello JM, Ortiz JA. J. Heterocycl. Chem. 1992; 29: 1557
• 14e Bihovsky R. J. Org. Chem. 1992; 57: 1029
• 15a Movassagh B, Sobhani S, Kheirdoush F, Fadaei Z. Synth. Commun. 2003; 33: 3103
• 15b Ranu BC, Mandal T. Can. J. Chem. 2006; 84: 762
• 15c Guo W, Chen J, Wu D, Ding J, Chen F, Wu H. Tetrahedron 2009; 65: 5240
• 15d Shailaja M, Manjula A, Rao BV. Synth. Commun. 2010; 40: 3629
• 16 Lee C.-F, Liu Y.-C, Badsara SS. Chem. Asian J. 2014; 9: 706
• 17a Taniguchi N. J. Org. Chem. 2004; 69: 6904
• 17b Wang L, Wang M, Huang F. Synlett 2005; 2007
• 17c Fukuzawa S.-i, Tanihara D, Kikuchi S. Synlett 2006; 2145
• 17d Gómez-Benítez V, Baldovino-Pantaleón O, Herrera-Álvarez C, Toscano RA, Morales-Morales D. Tetrahedron Lett. 2006; 47: 5059
• 17e Wu X.-M, Yan G.-B. Synlett 2015; 26: 537
• 17f Xu X, Wang W, Lu L, Zhang J, Luo J. Catal. Lett. 2022; 152: 3031
• 18a Hosseinian A, Ahmadi S, Hosseini Nasab FA, Mohammadi R, Vessally E. Top. Curr. Chem. 2018; 376: 39
• 18b Hazelton CJ, Iddon B, Suschitzky H, Woollew HL. J. Chem. Soc., Perkin Trans. 1 1992; 685
• 18c Yang Y, Dong W, Guo Y, Rioux RM. Green Chem. 2013; 15: 3170
• 18d Parumala SK. R, Peddinti RK. Green Chem. 2015; 17: 4068
• 18e Huang X, Chen Y, Zhen S, Song L, Gao M, Zhang P, Li H, Yuan B, Yang G. J. Org. Chem. 2018; 83: 7331
• 18f Gupta A, Rahaman A, Bhadra S. Org. Lett. 2019; 21: 6164
• 18g Yang D, Sun P, Wei W, Meng L, He L, Fang B, Jiang W, Wang H. Org. Chem. Front. 2016; 3: 1457
• 18h Jia X, Ma X, Feng W, Zhang J.-Q, Zhao Y, Guo B, Tang L, Yang Y.-Y. J. Org. Chem. 2022; 87: 16492
• 19a Cheng F, Sun Q, Lu J, Wang X, Zhang J. Chin. J. Org. Chem. 2023; 43: 3728
• 19b Yan G, Borah AJ, Wang L. Org. Biomol. Chem. 2014; 12: 9557
• 19c Zhu X, Xie X, Li P, Guo J, Wang L. Org. Lett. 2016; 18: 1546
• 19d Ye L.-M, Chen J, Mao P, Zhang X.-J, Yan M. Tetrahedron Lett. 2017; 58: 2743
• 19e Rathore V, Kumar S. Green Chem. 2019; 21: 2670
• 19f Groendyke BJ, Modak A, Cook SP. J. Org. Chem. 2019; 84: 13073
• 19g Kim J, Kang B, Hong SH. ACS Catal. 2020; 10: 6013
• 19h Kittikool T, Yotphan S. Eur. J. Org. Chem. 2020; 2020: 961
• 19i Wang X.-L, Bai X, Wu C.-F, Dong Y.-X, Zhang M, Fan L.-L, Tang L, Yang Y.-Y, Zhang J.-Q. Asian J. Org. Chem. 2021; 10: 386
• 19j Paul B, Das S, Chatterjee I. Org. Lett. 2023; 25: 653
• 19k Paul B, Das S, Chatterjee I. Org. Biomol. Chem. 2024; 22: 8133
• 20a Hoyle CE, Bowman CN. Angew. Chem. Int. Ed. 2010; 49: 1540
• 20b Hoogenboom R. Angew. Chem. Int. Ed. 2010; 49: 3415
• 20c Nair DP, Podgórski M, Chatani S, Gong T, Xi W, Fenoli CR, Bowman CN. Chem. Mater. 2014; 26: 724
• 21a Jones MW, Mantovani G, Ryan SM, Wang X, Brayden DJ, Haddleton DM. Chem. Commun. 2009; 5272
• 21b Taniguchi T, Fujii T, Idota A, Ishibashi H. Org. Lett. 2009; 11: 3298
• 21c Teders M, Henkel C, Anhäuser L, Strieth-Kalthoff F, Gómez-Suárez A, Kleinmans R, Kahnt A, Rentmeister A, Guldi D, Glorius F. Nat. Chem. 2018; 10: 981
• 22a Craine L, Raban M. Chem. Rev. 1989; 89: 689
• 22b Konovalova SA, Avdeenko AP, Santalova AA, Lysenko EN, Burmistrov KS. Russ. J. Org. Chem. 2016; 52: 1287
• 23a Davis FA, Friedman AJ, Kluger EW, Skibo EB, Fretz ER, Milicia AP, LeMasters WC. Bentley M. D, Lacadie JA, Douglass IB. J. Org. Chem. 1977; 42: 967
• 23b Klose J, Reese CB, Song Q. Tetrahedron 1997; 53: 14411
• 23c Sano T, Takagi T, Gama Y, Shibuya I, Shimizu M. Synthesis 2004; 1585
• 23d Taniguchi N. Synlett 2007; 1917
• 23e Peng Y, Lin Y, Nie R, Zheng Y, Liu Y, Guo L, Wu Y. Eur. J. Org. Chem. 2018; 2018: 844
• 23f Briggs EL, Tota A, Colella M, Degennaro L, Luisi R, Bull JA. Angew. Chem. Int. Ed. 2019; 58: 14303
• 24a Brill WK.-D, Nielsen J, Caruthers MH. J. Am. Chem. Soc. 1991; 113: 3972
• 24b Corey EJ, Chen Z, Tanoury GJ. J. Am. Chem. Soc. 1993; 115: 11000
• 24c Kaboudin B, Abedi Y, Kato J.-y, Yokomatsu T. Synthesis 2013; 45: 2323
• 24d Zhu Y, Chen T, Li S, Shimada S, Han L.-B. J. Am. Chem. Soc. 2016; 138: 5825
• 25a Mitra S, Mukherjee S, Sen SK, Hajra A. Bioorg. Med. Chem. Lett. 2014; 24: 2198
• 25b Xia M, Cheng J. Tetrahedron Lett. 2016; 57: 4702
• 25c Crocker RD, Hussein MA, Ho J, Nguyen TV. Chem. Eur. J. 2017; 23: 6259
• 25d Wang J, Wang X, Li H, Yan J. J. Organomet. Chem. 2018; 859: 75
• 26 Musiejuk M, Witt D. Org. Prep. Proced. Int. 2015; 47: 95
• 27a Swan JM. Nature 1957; 180: 643
• 27b Bao M, Shimizu M. Tetrahedron 2003; 59: 9655
• 27c Hunter R, Caira M, Stellenboom N. J. Org. Chem. 2006; 71: 8268
• 27d Antoniow S, Witt D. Synthesis 2007; 363
• 27e Szymelfejnik M, Demkowicz S, Rachon J, Witt D. Synthesis 2007; 3528
• 27f Vandavasi JK, Hu W.-P, Chen C.-Y, Wang J.-J. Tetrahedron 2011; 67: 8895
• 27g Taniguchi N. Tetrahedron 2017; 73: 2030
• 27h Dethe DH, Srivastava A, Dherange BD, Kumar BV. Adv. Synth. Catal. 2018; 360: 3020
• 27i Huang P, Wang P, Tang S, Fu Z, Lei A. Angew. Chem. Int. Ed. 2018; 57: 8115
• 27j Oka M, Katsube D, Tsuji T, Iida H. Org. Lett. 2020; 22: 9244
• 27k Spiliopoulou N, Kokotos CG. Green Chem. 2021; 23: 546
• 28a Koval’ IV. Russ. Chem. Rev. 1994; 63: 735
• 28b Chmielewski MM, Pires J. Org. Lett. 2008; 10: 837
• 28c Lee M, Tazzari V, Giustarini D, Rossi R, Sparatore A, Soldato PD, McGeer E, McGeer PL. J. Biol. Chem. 2010; 285: 17318
• 28d Mayer CD, Allmendinger L, Bracher F. Tetrahedron 2012; 68: 1810
• 29 Guo J, Zha J, Zhang T, Ding C.-H, Tan Q, Xu B. Org. Lett. 2021; 23: 3167
• 30a Ryu EK, Choe YS, Byun SS, Lee K.-H, Chi DY, Choi Y, Kim B.-T. Bioorg. Med. Chem. 2004; 12: 859
• 30b Chen S, Zhao X, Chen J, Chen J, Kuznetsova L, Wong SS, Ojima I. Bioconjugate Chem. 2010; 21: 979
• 30c Liu C, Pan J, Li S, Zhao Y, Wu LY, Berkman CE, Whorton AR, Xian M. Angew. Chem. Int. Ed. 2011; 50: 10327
• 31 McCulloch MW. B, Coombs GS, Banerjee N, Bugni TS, Cannon KM, Harper MK, Veltri CA, Virshup DM, Ireland CM. Bioorg. Med. Chem. 2009; 17: 2189
• 32a Arisawa M, Yamaguchi M. J. Am. Chem. Soc. 2003; 125: 6624
• 32b Tanaka K, Ajiki K. Tetrahedron Lett. 2004; 45: 5677
• 32c Caraballo R, Rahm M, Vongvilai P, Brinck T, Ramström O. Chem. Commun. 2008; 6603
• 32d Fritze UF, von Delius M. Chem. Commun. 2016; 52: 6363
• 32e Klepel F, Ravoo BJ. Org. Biomol. Chem. 2017; 15: 3840
• 32f Mathuri A, Pramanik M, Parida A, Mal P. Org. Biomol. Chem. 2021; 19: 8539
• 32g Lerma-Berlanga B, Orlando F, Merino E, Leyva-Pérez A. ChemCatChem 2024; 16: e202400909
• 33a Han M, Lee JT, Hahn H.-G. Tetrahedron Lett. 2011; 52: 236
• 33b Wang W, Lin Y, Ma Y, Tung C.-H, Xu Z. Org. Lett. 2018; 20: 3829
• 33c Zou J, Chen J, Shi T, Hou Y, Cao F, Wang Y, Wang X, Jia Z, Zhao Q, Wang Z. ACS Catal. 2019; 9: 11426
• 33d Li J, Li M, Duan X, Song W. Tetrahedron Lett. 2020; 61: 152256
• 34a Fang X, Bandarage UK, Wang T, Schroeder JD, Garvey DS. J. Org. Chem. 2001; 66: 4019
• 34b Zhang S, Zhao Y. J. Am. Chem. Soc. 2010; 132: 10642
• 34c Benincasa M. Eur. J. Med. Chem. 2015; 95: 210
• 34d Ajenjo J, Klepetářová B, Greenhall M, Bím D, Culka M, Rulíšek L, Beier P. Chem. Eur. J. 2019; 25: 11375
• 34e Zhu G.-Y, Zhou J.-J, Liu L.-G, Li X, Zhu X.-Q, Lu X, Zhou J.-M, Ye L.-W. Angew. Chem. Int. Ed. 2022; 61: e202204603
• 34f Li Z.-Y, Zhang X, Qian Y.-L, Du F.-S, Li Z.-C. J. Mater. Chem. B 2024; 12: 1569
• 35a Trofimov BA, Gusarova NK, Atavin AS, Amosova SV, Gusarov AV, Kazantseva NI, Kalabin GA. Zh. Org. Khim. 1973; 9: 8
• 35b Amosova SV, Potapov VA, Lasitsa NA. Russ. Chem. Bull. 1990; 39: 1069
• 36 Kabanyane ST, Magee DI. Can. J. Chem. 1992; 70: 2758
• 37a Deng K, Bensari A, Cohen T. J. Am. Chem. Soc. 2002; 124: 12106
• 37b Alcaraz M.-L, Atkinson S, Cornwall P, Foster AC, Gill DM, Humphries LA, Keegan PS, Kemp R, Merifield E, Nixon RA, Noble AJ, O’Beirne D, Patel ZM, Perkins J, Rowan P, Sadler P, Singleton JT, Tornos J, Watts AJ, Woodland IA. Org. Process Res. Dev. 2005; 9: 555
• 37c Chen W, Zhao X, Lu L, Cohen T. Org. Lett. 2006; 8: 2087
• 38a Trost BM, Salzmann TN, Hiroi K. J. Am. Chem. Soc. 1976; 98: 4887
• 38b Fujisawa T, Hata K, Kojima T. Chem. Lett. 1973; 2: 287
• 38c Huang B.-G, Kubiak GJ, Shay J, Pemberton C, Peers J, Hanna RG, Powers MR, Gamboa JA, Gelormini AM, Yarabe H, Rudisill DE. Org. Process Res. Dev. 2011; 15: 1040
• 38d Toledo FT, Marques H, Comasseto JV, Raminelli C. Tetrahedron Lett. 2007; 48: 8125
• 38e Matsuzawa T, Yoshida S, Hosoya T. Tetrahedron Lett. 2018; 59: 4197
• 39a Hiskey RG, Dennis AJ. J. Org. Chem. 1968; 33: 563
• 39b Hogg DR, Robertson A. J. Chem. Soc., Perkin Trans. 1 1979; 1125
• 40a Humphrey RE, Hawkins JM. Anal. Chem. 1964; 36: 1812
• 40b Levison ME, Josephson AS, Kirschenbaum DM. Experientia 1969; 25: 126
• 41a Davis FA, Friedman AJ, Nadir UK. J. Am. Chem. Soc. 1978; 100: 2844
• 41b Trost BM, Ochiai M, McDougal PG. J. Am. Chem. Soc. 1978; 100: 7103
• 41c Caserío MC, Fisher CL, Kim JK. J. Org. Chem. 1985; 50: 4390
• 41d Ni Y, Zuo H, Li Y, Wu Y, Zhong F. Org. Lett. 2018; 20: 4350
• 42a Yamagiwa N, Suto Y, Torisawa Y. Bioorg. Med. Chem. Lett. 2007; 17: 6197
• 42b Kondo T, Uenoyama S, Fujita K, Mitsudo T. J. Am. Chem. Soc. 1999; 121: 482
• 43a Gareau Y, Orellana A. Synlett 1997; 803
• 43b Ogawa A, Kuniyasu H, Sonoda N, Hirao T. J. Org. Chem. 1997; 62: 8361
• 43c Arisawa M, Yamaguchi M. Org. Lett. 2001; 3: 763
• 43d Guo Y.-J, Tang R.-Y, Li J.-H, Zhong P, Zhang X.-G. Adv. Synth. Catal. 2009; 351: 2615
• 43e Taniguchi N. Tetrahedron 2009; 65: 2782
• 43f Ananikov VP, Gayduk KA, Orlov NV, Beletskaya IP, Khrustalev VN, Antipin MY. Chem. Eur. J. 2010; 16: 2063
• 44a Comprehensive Organic Chemistry, 3rd ed. Barton D, Ollis W. Pergamon; Oxford: 1979
• 44b Taniguchi N. Synlett 2005; 1687
• 44c Kiasat AR, Mokhtari B, Kazemi F, Yousefi S, Javaherian M. J. Sulfur Chem. 2007; 28: 171
• 44d Jiang Y, Qin Y, Xie S, Zhang X, Dong J, Ma D. Org. Lett. 2009; 11: 5250
• 44e Taniguchi N. Tetrahedron 2012; 68: 10510
• 44f Chen HY, Peng WT, Lee YH, Chang YL, Chen YJ, Lai YC, Jheng NY, Chen HY. Organometallics 2013; 32: 5514
• 44g Li Z, Ke F, Deng H, Xu H, Xiang H, Zhou X. Org. Biomol. Chem. 2013; 11: 2943
• 44h Rostami A, Rostami A, Iranpoor N, Zolfigol MA. Tetrahedron Lett. 2016; 57: 192
• 44i Soleiman-Beigi M, Mohammadi F. Catal. Lett. 2016; 146: 1497
• 44j Nguyen TB. Adv. Synth. Catal. 2017; 359: 1066
• 45a Organic Chemistry of Sulfur . Oae S. Plenum; New York: 1975
• 45b Hase TA, Peräkylä H. Synth. Commun. 1982; 12: 947
• 45c Dhar P, Chandrasekaran S. J. Org. Chem. 1989; 54: 2998
• 45d Sonavane SU, Chidambaram M, Almog J, Sasson Y. Tetrahedron Lett. 2007; 48: 6048
• 45e Polshettiwar V, Nivsarkar M, Acharya J, Kaushik MP. Tetrahedron Lett. 2003; 44: 887
• 45f Sengupta D, Basu B. Tetrahedron Lett. 2013; 54: 2277
• 45g Abbasi M, Mohammadizadeh MR, Saeedi N. New J. Chem. 2016; 40: 89
• 46a Soleiman-Beigi M, Mohammadi F. Tetrahedron Lett. 2012; 53: 7028
• 46b Abbasi M, Mohammadizadeh MR, Taghavi ZK. J. Iran. Chem. Soc. 2013; 10: 201
• 46c Nowrouzi N, Abbasi M, Shaikhi Shahidzadeh E. Appl. Organomet. Chem. 2023; 37: e6941
• 46d Kim K, Shin Y, Chae J. Synlett 2024; 35: 826
• 47a Numata T, Awano H, Oae S. Tetrahedron Lett. 1980; 21: 1235
• 47b Olah GA, Narang SC, Field LD, Salem GF. J. Org. Chem. 1980; 45: 4792
• 47c Olah GA, Narang SC, Field LD, Karpeles R. J. Org. Chem. 1981; 46: 2408
• 47d Firouzabadi H, Karimi B. Synthesis 1999; 500
• 47e Huang Y, Guo H, Zhang Y, Wang Y. J. Chem. Res., Synop. 1999; 214
• 47f He Y, Jiang J, Bao W, Deng W, Xiang J. Tetrahedron Lett. 2017; 58: 4583
• 47g Jafarpour M, Rezaeifard A, Heidari M. Phosphorus, Sulfur Silicon Relat. Elem. 2011; 186: 1470
• 47h Kumar H, Dubey A, Prajapati G, Kant R, Ampapathi RS, Mandal PK. New J. Chem. 2022; 46: 3426
• 48a Fujimori K, Togo H, Oae S. Tetrahedron Lett. 1980; 21: 4921
• 48b Palumbo G, Parrilli M, Neri O, Ferreri C, Caputo R. Tetrahedron Lett. 1982; 23: 2391
• 48c Suzuki H, Tani H, Osuka A. Chem. Lett. 1984; 13: 139
• 48d Yadav A, Kumar R, Prasad V. Synthesis 2024; 56: 1923
• 49a Pinnick HW, Reynolds MA, McDonald RT. Jr, Brewster WD. J. Org. Chem. 1980; 45: 930
• 49b Dhar P, Ranjan R, Chandrasekaran S. J. Org. Chem. 1990; 55: 3728
• 49c Liang S, Hofman K, Friedrich M, Manolikakes G. Eur. J. Org. Chem. 2020; 2020: 4664
• 50a Yoshida Z, Okushi T, Manabe O. Tetrahedron Lett. 1970; 11: 1641
• 50b Lalancette JM, Frêche A, Brindle JR, Laliberté M. Synthesis 1972; 526
• 50c Bandgar BP, Uppalla LS, Sadavarte VS. Tetrahedron Lett. 2001; 42: 6741
• 50d Korn TJ, Knochel P. Synlett 2005; 1185
• 50e Prabhu KR, Ramesha AR, Chandrasekaran S. J. Org. Chem. 1995; 60: 7142
• 50f Sureshkumar D, Gunasundari T, Ganesh V, Chandrasekaran S. J. Org. Chem. 2007; 72: 2106
• 50g Iranpoor N, Firouzabadi H, Chitsazi M, Jafari AA. Tetrahedron 2002; 58: 7037
• 50h Wessig P, Gerngroß M, Freyse D, Bruhns P, Przezdziak M, Schilde U, Kelling A. J. Org. Chem. 2016; 81: 3, 1125