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DOI: 10.1055/s-0037-1610354
Selenosilane-Promoted Selective Mild Transformation of N-Thiophthalimides into Symmetric Disulfides
Publication History
Received: 22 October 2018
Accepted after revision: 13 November 2018
Publication Date:
07 January 2019 (online)
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Abstract
The reactivity of N-thiophthalimides with silyl chalcogenides is described. Treatment of N-thiophthalimides with bis(trimethylsilyl) sulfide [(Me3Si)2S] leads to the formation of a mixture of the corresponding disulfides and trisulfides. On the other hand, N-thiophthalimides react with bis(trimethylsilyl) selenide [(Me3Si)2Se] under TBAF catalysis to smoothly give variously substituted diaryl, divinyl, and dialkyl disulfides; formation of a selenotrisulfide (dithiaselane, RSSeSR) is rationalized as an intermediate. Exploiting the different chemical behavior of silyl chalcogenides, we have disclosed a novel, selective, and operationally simple method to access disulfides in good yields under mild conditions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610354.
- Supporting Information
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References
- 1a Musiejuk M, Witt D. Org. Prep. Proced. Int. 2015; 47: 95
- 1b Mandal B, Basu B. RSC Adv. 2014; 4: 13854
- 1c Kondo T, Mitsudo T. Chem. Rev. 2000; 100: 3205
- 1d Metzner P, Thuillier A. Sulfur Reagents in Organic Synthesis . Katritzky AR. Academic Press; San Diego: 1994
- 2a Xiao X, Xue J, Jiang X. Nat. Commun. 2018; 9: 2191
- 2b Block E. In Garlic and Other Allium: The Lore and the Science . Royal Society of Chemistry; Cambridge: 2010
- 3a Tanini D, Tiberi C, Gellini C, Salvi PR, Capperucci A. Adv. Synth. Catal. 2018; 360: 3367
- 3b Tanini D, Grechi A, Dei S, Teodori E, Capperucci A. New J. Chem. 2018; 42: 6077
- 3c Menichetti S, Capperucci A, Tanini D, Braga AL, Botteselle GV, Viglianisi C. Eur. J. Org. Chem. 2016; 3097
- 3d Capperucci A, Tanini D. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190: 1320
- 3e Tanini D, Panzella L, Amorati R, Capperucci A, Pizzo E, Napolitano A, Menichetti S, d’Ischia M. Org. Biomol. Chem. 2015; 13: 5757
- 3f Tanini D, Capperucci A, Degl’Innocenti A. Eur. J. Org. Chem. 2015; 357
- 3g Capperucci A, Tanini D, Borgogni C, Degl’Innocenti A. Heteroat. Chem. 2014; 25: 678
- 4 Capperucci A, Degl’Innocenti A, Funicello M, Mauriello G, Scafato P, Spagnolo P. J. Org. Chem. 1995; 60: 2254
- 5a Harpp DN, Friedlander BT, Larsen C, Steliou K, Stockton A. J. Org. Chem. 1978; 43: 3481
- 5b Armitage DA, Clark MJ, Tso CC. J. Chem. Soc., Perkin Trans. 1 1972; 680
- 6a Capozzi G, Capperucci A, Degl’Innocenti A, Del Duce R, Menichetti S. Gazz. Chim. Ital. 1990; 120: 421
- 6b Capozzi G, Capperucci A, Degl’Innocenti A, Del Duce R, Menichetti S. Tetrahedron Lett. 1989; 30: 2995
- 7a Boustany K, Sullivan BA. Tetrahedron Lett. 1970; 11: 3457
- 7b Harpp DN, Back GT. J. Org. Chem. 1971; 36: 3828
- 8a Harpp DN, Back GT. Tetrahedron Lett. 1971; 12: 4953
- 8b Bures J, Isart C, Vilarrasa J. Org. Lett. 2007; 9: 4635
- 9 Nicolaou KC, Hummel CW, Pitsinos EN, Nakada M, Smith AL, Shibayama K, Saimoto H. J. Am. Chem. Soc. 1992; 114: 10082
- 10 Denmark SE, Juanet A. J. Org. Chem. 2014; 79: 140 ; and references cited therein
- 11a Wang C, Yang X, Loh CC. J, Raabe G, Enders D. Chem.–Eur. J. 2012; 18: 11531
- 11b Cai Y, Li J, Chen W, Xie M, Liu X, Lin L, Feng X. Org. Lett. 2012; 14: 2726
- 11c Li X, Liu C, Xue XS, Cheng JP. Org. Lett. 2012; 14: 4374
- 12a Silveira CC, Mendes SR, Wolf L, Martins GM. Tetrahedron Lett. 2010; 51: 2014
- 12b Tudge M, Tamiya M, Savarin C, Humphrey GR. Org. Lett. 2006; 8: 565
- 12c Marcantoni E, Cipolletti R, Marsili L, Menichetti S, Properzi R, Viglianisi C. Eur. J. Org. Chem. 2013; 132
- 13a Busi E, Capozzi G, Menichetti S, Nativi C. Synthesis 1992; 643
- 13b Capozzi G, De Sio F, Menichetti S, Nativi C, Pacini PL. Synthesis 1994; 521
- 13c Viglianisi C, Faggi C, Piantini S, Procacci P, Becucci L, Menichetti S. J. Org. Chem. 2013; 78: 3496
- 14a Capozzi G, Menichetti S, Nativi C, Rosi A, Valle G. Tetrahedron 1992; 48: 9023
- 14b Capozzi G, Franck RG. W, Mattioli M, Menichetti S, Nativi C, Valle G. J. Org. Chem. 1995; 60: 6416
- 15a Capozzi G, Falciani C, Menichetti S, Nativi C. J. Org. Chem. 1997; 62: 2611
- 15b Amorati R, Catarzi F, Menichetti S, Pedulli GF, Viglianisi C. J. Am. Chem. Soc. 2008; 130: 237
- 15c Menichetti S, Amorati R, Meoni V, Tofani L, Caminati G, Viglianisi C. Org. Lett. 2016; 18: 5464
- 16a Lamanna G, Faggi C, Gasparrini F, Ciogli A, Villani C, Stephens PL, Devlin FL, Menichetti S. Chem.–Eur. J. 2008; 14: 5747
- 16b Menichetti S., Faggi C., Onori M., Piantini S., Ferreira M., Rocchi S., Lupi M., Marin I., Maggini M., Viglianisi C.; Eur. J. Org. Chem.; DOI: 10.1002/ejoc.201801493.
- 17a Fleischer H, Glang S, Schollmeyer D, Mitzel NW, Bühl M. Dalton Trans. 2004; 3765
- 17b Kice JL, Lee TW. S, Pan S.-t. J. Am. Chem. Soc. 1980; 102: 4448
- 17c Ganther HE. Biochemistry 1971; 10: 4089
- 18 In the case of compound 4j, the reaction required shorter time (45 min. vs. 2 h), in order to avoid decomposition of the disulfide.
- 19 Capozzi G, Falciani C, Menichetti S, Nativi C. Gazz. Chim. Ital. 1996; 126: 227 ; product CAS number: 42521-82-4
- 20 Pappalardo S, Bottino F. J. Chem. Soc., Perkin Trans. 2 1984; 1001 ; product CAS number: 14665-49-7
- 21 Kmoníček V, Holubek J, Svátek E, Metyšová J, Protiva M. Collect. Czech. Chem. Commun. 1987; 52: 793 ; product CAS number: 5397-29-5
- 22 Vyas R, Chanda B, Sudalai A. Chem. Lett. 1998; 43
- 23a Inter alia: Zhang W.-J, Huang K.-J. Inorg. Chem. Front. 2017; 4: 1602
- 23b Matxain JM, Asua JM, Ruipérez F. PhysChemChemPhys 2016; 18: 1758
- 23c Canadell J, Goossens H, Klumperman B. Macromolecules 2011; 44: 2536
- 24a Mlostoń G, Capperucci A, Tanini D, Hamera-Fałdyga R, Heimgartner H. Eur. J. Org. Chem. 2017; 6831
- 24b Habibi A, Baghersad MH, Bilabary M, Valizadeh Y. Tetrahedron Lett. 2016; 57: 559
- 24c Soleiman-Beigi M, Hemmati M. Appl. Organometal. Chem. 2013; 27: 734
- 24d Firouzabadi H, Iranpoor N, Abbasi M. Tetrahedron Lett. 2010; 51: 508
- 24e Kelly CB, Lee C, Leadbeater NE. Tetrahedron Lett. 2011; 52: 4587
- 24f Sonavane SU, Chidambaram M, Almog J, Sasson Y. Tetrahedron Lett. 2007; 48: 6048
- 24g Li C.-X, Liu R.-J, Yin K, Wen L.-R, Li M. Org. Biomol. Chem. 2017; 15: 5820
- 25a Detty MR, Seidler MD. J. Org. Chem. 1982; 47: 1354
- 25b The reported procedure was slightly modified. Instead of a distillation, the crude material was purified by filtration on a short pad of Celite.
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