33.1. 8.2 Alk-1-enyl Sulfides (Update 2024)
Book
Editors: Campagne, J.-M. ; Donohoe, T. J.; Drabowicz, J. ; Fuerstner, A. ; Jiang, X. ; Wang, M. ; Wirth, T.
Title: Knowledge Updates 2024/3
Online ISBN: 9783132457089; Book DOI: 10.1055/b000000969
1st edition © 2024 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
Alk-1-enyl sulfides are an interesting class of compounds that are widely used in organic synthesis. There are a large variety of methods for their preparation, employing both substrates and reagents as the sulfur source. Most recent advances (in the period 2006–2022) reported for the synthesis of alk-1-enyl sulfides have involved the preparation of variously substituted derivatives of the title compounds. The substituents include halogens (fluorine and polyfluoroalkyls, chlorine, bromine, and iodine), the nitro group, and acyloxy, ester, carboxy, sulfonyl, and amino groups. The application of various sulfur sources and synthetic strategies to form alk-1-enyl sulfides, and finally the synthesis of cyclic alk-1-enyl sulfides and polyene alk-1-enyl sulfides are also reported.
Key words
alkenyl sulfides - polyenyl sulfides - alkenes - alkynes - sulfanylation of alkynes - perhalogenoalkenes - thiols - palladium catalysis - copper catalysis - gold catalysis - ruthenium catalysis - dithioesters - carbon disulfide - isothiocyanates - sulfonothioates - β-sulfinyl esters - thiirenium ions - electrochemical cross-coupling reactions- 2 Velasco N, Virumbrales C, Sanz R, Suárez-Pantiga S, Fernández-Rodríguez MA. Org. Lett. 2018; 20: 2848
- 12 Higashimae S, Kurata D, Kawaguchi S, Kodama S, Sonoda M, Nomoto A, Ogawa A. J. Org. Chem. 2018; 83: 5267
- 19 Di Giuseppe A, Castarlenas R, Pérez-Torrente JJ, Crucianelli M, Polo V, Sancho R, Lahoz FJ, Oro LA. J. Am. Chem. Soc. 2012; 134: 8171
- 23 Wang J, Zhang S, Xu C, Wojtas Ł, Akhmedov NG, Chen H, Shi X. Angew. Chem. Int. Ed. 2018; 57: 6915
- 24 Gogoi MP, Vanjari R, Prabagar B, Yang S, Dutta S, Mallick RK, Gandon V, Sahoo AK. Chem. Commun. (Cambridge) 2021; 57: 7521
- 25 Wang J, Xiong H.-Y, Petit E, Bailly L, Pannecoucke X, Poisson T, Besset T. Chem. Commun. (Cambridge) 2019; 55: 8784
- 28 Wang J, Jia S, Okuyama K, Huang Z, Tokunaga E, Sumii Y, Shibata N. J. Org. Chem. 2017; 82: 11 939
- 31 Ren S, Xue B, Zheng T, Wang Y, Sun H, Li X, Fuhr O, Fenske D. Appl. Organomet. Chem. 2020; 34: e5291
- 33 Shimizu A, Horiuchi S, Hayashi R, Matsumoto K, Miyamoto Y, Morisawa Y, Wakabayashi T, Yoshida J. ARKIVOC 2018; ii, 97 available online at www.arkat-usa.org/
- 39 Makarov VA, Braun H, Richter M, Riabova OB, Kirchmair J, Kazakova ES, Seidel N, Wutzler P, Schmidtke M. ChemMedChem 2015; 10: 1629
- 42 Petrova OV, Sagitova EF, Ushakov IA, Sobenina LN, Mikhaleva AI, Trofimov BA. J. Sulfur Chem. 2015; 36: 145
- 43 Sobenina LN, Mikhaleva AI, Sergeeva MP, Petrova OV, Aksamentova TN, Kozyreva OB, Toryashinova DSD, Trofimov BA. Tetrahedron 1995; 51: 4223
- 51 Ibiş C, Beyazit N. ARKIVOC 2010; ix, 244 available online at www.arkat-usa.org/
- 56 Aydinli SG, Ozdamar Y, Sayil C, Deniz NG, Stasevych M, Zvarych V, Komarovska-Porokhnyavets O, Novikov V. Synth. Commun. 2020; 50: 3234
- 64 Ibis C, Ayla SS, Yavuz Ş, Asar H, Özkök F, Bahar H. Phosphorus, Sulfur Silicon Relat. Elem. 2018; 193: 358