A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

Doaa Ali; Yasien Amer; Wade F. Petersen; Catherine H. Kaschula; Roger Hunter

doi:10.1055/s-0040-1706018

SynOpen, Inhaltsverzeichnis

CC BY-NC-ND 4.0 · SynOpen 2021; 05(01): 49-64
DOI: 10.1055/s-0040-1706018

review

A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

Doaa Ali

^aDepartment of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

^bDepartment of Chemistry and Polymer Science, Stellenbosch University, Stellenbosch 7600, South Africa

,

Yasien Amer

^aDepartment of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

,

Wade F. Petersen

^aDepartment of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

,

Catherine H. Kaschula

^bDepartment of Chemistry and Polymer Science, Stellenbosch University, Stellenbosch 7600, South Africa

,

Roger Hunter ∗

^aDepartment of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

› Institutsangaben

Abstract

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Abstract

It has been ten years since the last comprehensive review on polysulfanes, and during the intervening period, organodi-, organotri- and organotetrasulfanes have featured prominently in both the chemistry and biology literature. This timely update presents both a mechanistic and historical account of synthesis methodology available for organotri- and organotetrasulfanes involving heterolytic S–S bond formation.

Key words

organotrisulfane - organotetrasulfane - sulfur-sulfur bond - trisulfide - tetrasulfide

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Referenzen

References

1a Clennan EL, Stensaas KL. Org. Prep. Proced. Int. 1998; 30: 551
1b Steudel R. Chem. Rev. 2002; 102: 3905
1c Atwood DA, Zaman MK. Sulfur: Organic Polysulfanes. In Encyclopedia Inorg. Bioinorg. Chem. Wiley; Weinheim: 2011.

For an updated version of this article, see also:

1d Steudel R. Sulfur: Organic Polysulfanes. In Encyclopedia Inorg. Bioinorg. Chem. Wiley; Weinheim: 2011.

2 Kim J, Movassaghi M. J. Am. Chem. Soc. 2010; 132: 14376

3a Cerda MM, Hammers MD, Earp MS, Zakharov LN, Pluth MD. Org. Lett. 2017; 19: 2314
3b Filipovic MR, Zivanovic J, Alvarez B, Banerjee R. Chem. Rev. 2018; 118: 1253

4 Khongorzul P, Ling CJ, Khan FU, Ihsan AU, Zhang J. Mol. Cancer Res. 2020; 18: 3
5 Wang D.-Y, Guo W, Fu Y. Acc. Chem. Res. 2019; 52: 2290

6a Mandal B, Basu B. RSC Adv. 2014; 4: 13854
6b Musiejuk M, Witt D. Org. Prep. Proced. Int. 2015; 47: 95
6c Wang M, Jiang X. Top. Curr. Chem. 2018; 376: 14

7a Strecker W. Ber. Dtsch. Chem. Ges. 1908; 41: 1105
7b See also: Fehér F, Krause G, Vogelbruch K. Chem. Ber. 1957; 90: 1570

8 Riding RW, Thomas JS. J. Chem. Soc., Trans. 1923; 123: 3271

9a Filipponen I, Guerra A, Hai A, Lucia LA, Argyropoulos DS. Ind. Eng. Chem. Res. 2006; 45: 7388
9b Amrani A, Kamyshny AJr, Lev O, Aizenshtat Z. J. Inorg. Chem. 2006; 45: 1427

10a Fuson RC, Price CC, Burness DM, Foster RE, Hatchard WR, Lipscomb RD. Levinstein. J. Org. Chem. 1946; 11: 487
10b Salivon NF, Filinchuk YE, Olijnyk VV. Z. Anorg. Allg. Chem. 2006; 62: 1610

11 Dannley RL, Zazaris DA. Can. J. Chem. 1965; 43: 2610

12a Morel G, Marchand E, Foucand A. Synthesis 1980; 918
12b Korchevin NA, Turchaninova LP, Deryagina EN, Voronkov MG. Zh. Obshch. Khim. 1989; 59: 1785
12c Deryagina EN, Kozlov IA, Vershal VV, Babkin VA. Zh. Obshch. Khim. 1996; 66: 1279

13 Nobuo Y, Mutsuhisa F, Masayuki N, Toshikazu T. Chem. Lett. 2002; 31: 454
14 Sinha P, Kundu A, Roy S, Prabhakar S, Vairamani M. Organometallics 2001; 20: 157
15 Labuk P, Duda A, Penczek S. Phosphorus, Sulfur Silicon Relat. Elem. 1989; 42: 107
16 Ahrika A, Robert J, Anouti M, Paris J. Acta Chem. Scand. 1999; 53: 513
17 Baker A, Graz M, Saunders R, Evans GJ. S, Kaul S, Wirth T. J. Flow Chem. 2013; 3: 118
18 Zheng S, Liao M, Chen Y, Brook MA. Green Chem. 2020; 22: 94
19 Milligan B, Saville B, Swan JM. J. Chem. Soc. 1961; 4850
20 Milligan B, Saville B, Swan JM. J. Chem. Soc. 1963; 3608
21 Bunte H. Ber. Dtsch. Chem. Ges. 1874; 7: 646
22 Qiao Z, Jiang X. Org. Biomol. Chem. 2017; 15: 1942
23 Bhattacherjee D, Sufian A, Mahato SK, Begum S, Banerjee K, De S, Srivastava HK, Bhabak KP. Chem. Commun. 2019; 55: 13534
24 Milligan B, Swan JM. J. Chem. Soc. 1965; 2901
25 Buckman JD, Field L. J. Org. Chem. 1967; 32: 454

26a Fehér F, Berthold HJ. Chem. Ber. 1955; 88: 1634
26b Pitombo LR. M. Chem. Ber. 1962; 95: 2960
26c Wilson RM, Buchanan DN. In Methodicum Chimicum, Vol. 7, Chap. 33. Zimmer H, Niedenzu K. Thieme; New York: 1976
26d Gunderman KD, Hümke K. In Methoden der Organischen Chemie, Vol. E 11 (Teilband 1). Klamann D. Thieme; Stuttgart: 1985: 148
26e Munavalli S, Muller AJ, Rossman DI, Rohrbaugh DK, Ferguson CP. J. Fluorine Chem. 1994; 67: 37

27 Capozzi G, Capperucci A, Degl’Innocenti A, Del Duce R, Menichetti S. Tetrahedron Lett. 1989; 30: 2991
28 Viglianisi C, Bonardi C, Ermini E, Capperucci A, Menichetti S, Tanini D. Synthesis 2019; 51: 1819
29 Harpp DN, Gingras M, Aida T, Chan TH. Synthesis 1987; 1122
30 Steudel R, Pridöhl M, Buschmann J, Luger P. Chem. Ber. 1995; 128: 725
31 Chakravarti GC. J. Chem. Soc., Trans. 1923; 123: 964
32 Clayton JO, Etzler DH. J. Am. Chem. Soc. 1947; 69: 974
33 Nakabayashi T, Tsurugi J, Yabuta T. J. Org. Chem. 1964; 29: 1236
34 Bloch I, Bergmann M. Ber. Dtsch. Chem. Ges. 1920; 53: 961
35 Twiss D. J. Am. Chem. Soc. 1927; 49: 491
36 Fehér F, Weber H. Chem. Ber. 1958; 91: 642
37 Abel EW, Armitage DA. J. Chem. Soc. 1964; 5975
38 Wardell JL, Clarke PL. J. Organomet. Chem. 1971; 26: 345
39 Steudel R, Kustos M, Münchow V, Westphal U. Chem.Ber./Recl. 1997; 130: 757
40 Barany G, Mott AW. J. Org. Chem. 1984; 49: 1043
41 Harpp DN, Derbesy G. Tetrahedron Lett. 1994; 35: 5381
42 Czepukojc B, Viswanathan UM, Raza A, Ali S, Burkholz T, Jacob C. Phosphorus, Sulfur Silicon Relat. Elem. 2013; 188: 446
43 Rezkallah D, Schwind L, Abuasali I, Nasim J, Jacob C, Gotz C, Montenarh M. Int. J. Oncol. 2015; 47: 991
44 Zysman-Colman E, Harpp DN. J. Org. Chem. 2003; 68: 2487
45 Kresze G, Patzschke H. Chem. Ber. 1960; 93: 380
46 Sullivan AB, Boustany K. Int. J. Sulfur Chem., Part A 1971; 1: 207

47a Harpp DN, Ash DK. Int. J. Sulfur Chem., Part A 1971; 1: 57
47b Harpp DN, Ash DK. Int. J. Sulfur Chem., Part A 1971; 1: 211
47c Harpp DN, Back TG. Tetrahedron Lett. 1972; 1481

48 Naik KG. J. Chem. Soc., Trans. 1921; 119: 1166
49 Kalnins MV. Can. J. Chem. 1966; 44: 2111
50 Harpp DN, Steliou K, Chan TH. J. Am. Chem. Soc. 1978; 100: 1222
51 Harpp DN, Smith RA, Steliou K. J. Org. Chem. 1981; 46: 2072
52 Banerji A, Kalena GP. Tetrahedron Lett. 1980; 21: 3003
53 An H, Zhu J, Wang X, Xu X. Bioorg. Med. Chem. Lett. 2006; 16: 4826
54 Mott AW, Barany G. Synthesis 1984; 657

55a Vineyard BD. J. Org. Chem. 1966; 31: 601
55b Vineyard BD. J. Org. Chem. 1967; 32: 3833

56 Gaensslen M, Minkwitz R, Molzbeck W, Oberhammer H. Inorg. Chem. 1992; 31: 4147
57 Gombler W, Seel F. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1975; 30: 169
58 Zack NR, Shreeve JM. Inorg. Nucl. Chem. Lett. 1974; 10: 619

59a Park C.-M, Weerasinghe L, Day JJ, Fukuto JM, Xian M. Mol. BioSyst. 2015; 11: 1775
59b Bora P, Chauhan P, Pardeshi KA, Chakrapani H. RSC Adv. 2018; 8: 27359
59c Benchoam D, Cuevasanta E, Möller MN, Alvarez B. Antioxidants 2019; 8: 48

60 Böhme H, Zinner G. Justus Liebigs Ann. Chem. 1954; 585: 142
61 Kang J, Ferrell AJ, Chen W, Wang D, Xian M. Org. Lett. 2018; 20: 852
62 Nakabayashi T, Tsurugi J. J. Org. Chem. 1961; 26: 2482
63 Kharasch N, Potempa SJ, Wehrmeister HL. Chem. Rev. 1946; 39: 269
64 Thea S, Cevasco G. Tetrahedron Lett. 1988; 29: 2865
65 Kawamura S, Abe Y, Tsurugi J. J. Org. Chem. 1969; 34: 3633
66 Xiao X, Feng M, Jiang X. Angew. Chem. Int. Ed. 2016; 55: 14121
67 Takano S, Hiroya K, Ogasawara K. Chem. Lett. 1983; 12: 255
68 Fujiki K, Tanifuji N, Sasaki Y, Yokoyama T. Synthesis 2002; 343
69 Harpp DN, Ash DK, Back TG, Gleason JG, Orwig BA, VanHorn WF, Snyder JP. Tetrahedron Lett. 1970; 3551
70 Harpp DN, Granata A. Tetrahedron Lett. 1976; 3001
71 Bailey TS, Zakharov LN, Pluth MD. J. Am. Chem. Soc. 2014; 136: 10573
72 Lach S, Witt D. Synlett 2013; 24: 1927
73 Xu S, Wang Y, Radford MN, Ferrell AJ, Xian M. Org. Lett. 2018; 20: 465
74 Ali D, Hunter R, Kaschula CH, De Doncker S, Rees-Jones SC. M. J. Org. Chem. 2019; 84: 2862
75 Bolton SG, Cerda MM, Gilbert AK, Pluth MD. Free Radical Biol. Med. 2019; 131: 393
76 Lach S, Witt D. Heteroat. Chem. 2014; 25: 10
77 Böhme H, Clement M. Justus Liebigs Ann. Chem. 1952; 576: 61
78 Bohme H, van Ham G. Justus Liebigs Ann. Chem. 1958; 617: 62
79 Fehér F, Kruse W. Chem. Ber. 1958; 91: 2528
80 Williams CR, Britten JF, Harpp DN. J. Org. Chem. 1994; 59: 806

81a Rys AZ, Harpp DN. Tetrahedron Lett. 2000; 41: 7169
81b Hou Y, Abu-Yousef IA, Harpp DN. Tetrahedron Lett. 2000; 41: 7809
81c Hou Y, Abu-Yousef IA, Doung Y, Harpp DN. Tetrahedron Lett. 2001; 42: 8607
81d Abu-Yousef I, Rys AZ, Harpp DN. J. Sulfur Chem. 2006; 27: 15
81e Abu-Yousef IA, Rys AZ, Harpp DN. J. Sulfur Chem. 2007; 28: 251
81f For insertion of sulfur into polysulfanes using a Rh(I) catalyst, see: Arisawa M, Tanaka K, Yamaguchi M. Tetrahedron Lett. 2005; 46: 4797

82 Lach S, Sliwka-Kaszynska M, Witt D. Synlett 2010; 2857
83 Wang W, Lin Y, Ma Y, Tung C.-H, Xu Z. Org. Lett. 2018; 20: 3829
84 Xiao X, Xue J, Jiang X. Nat. Commun. 2018; 9: 2191
85 Haseltine JN, Cabal MP, Mantlo NB, Iwasawa N, Yamashita DS, Coleman RS, Danishefsky SJ, Schulte GK. J. Am. Chem. Soc. 1991; 113: 3850
86 Nicolaou KC, Li R, Lu Z, Pitsinos EN, Alemany LB, Aujay M, Lee C, Sandoval J, Gavrilyuk J. J. Am. Chem. Soc. 2018; 140: 12120
87 Harpp DN, Friedlander BT, Larsen C, Steliou K, Stockton A. J. Org. Chem. 1978; 43: 3481
88 Ercole F, Whittaker MR, Halls ML, Boyd BJ, Davis TP, Quinn JF. Chem. Commun. 2017; 53: 8030

89a Harpp DN, Ash DK, Smith RA. J. Org. Chem. 1979; 44: 4135
89b Williams CR, Macdonald JG, Harpp DN, Steudel R, Foerster S. Sulfur Lett. 1992; 13: 247

90 Xue J, Jiang X. Nat. Commun. 2020; 11: 4170
91 Kagami H, Motoki S. J. Org. Chem. 1977; 42: 4139
92 Xue J, Jiang X. Org. Lett. 2020; 22: 8044
93 Oka M, Katsube D, Tsuji T, Iida H. Org. Lett. 2020; 22: 9244

94a Qiu X, Yang X, Zhang Y, Song S, Jiao N. Org. Chem. Front. 2019; 6: 2220
94b Song L, Li W, Duan W, An J, Tang S, Li L, Yang G. Green Chem. 2019; 21: 1432

95 Li X.-B, Li Z.-J, Gao Y.-J, Meng Q.-Y, Yu S, Weiss RG, Tung C.-H, Wu L.-Z. Angew. Chem. Int. Ed. 2014; 53: 2085 ; Angew. Chem. 2014, 126, 2117
96 Huang P, Wang P, Tang S, Fu Z, Lei A. Angew. Chem. Int. Ed. 2018; 57: 8115 ; Angew. Chem. 2018, 130, 8247
97 Wu Z, Pratt DA. J. Am. Chem. Soc. 2020; 142: 10284