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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 20
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Articles

The oxysulfenylation of alkenes with dimethyl sulfoxide/oxalyl chloride

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Pages 2662-2670 | Received 22 Feb 2019, Published online: 15 Jul 2019

References

  • Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S. A.; Liu, X. Recent Advances in C-S Bond Formation via C-H Bond Functionalization and Decarboxylation. Chem. Soc. Rev. 2015, 44, 291–314. DOI: 10.1039/c4cs00239c.
  • Beletskaya, I. P.; Ananikov, V. P. Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions. Chem. Rev. 2011, 111, 1596–1636. DOI: 10.1021/cr100347k.
  • Fontecave, M.; Ollagnier-de-Choudens, S.; Mulliez, E. Biological Radical Sulfur Insertion Reactions. Chem. Rev. 2003, 103, 2149–2166. DOI: 10.1021/cr020427j.
  • Kondo, T.; Mitsudo, T.-A. Metal-Catalyzed Carbon-Sulfur Bond Formation. Chem. Rev. 2000, 100, 3205–3220. DOI: 10.1021/cr9902749.
  • Zhang, R.; Yan, Z.; Lin, S. Strategy for Constructing Sulfenylated 2, 3-Dihydrobenzofurans and β-Acetoxy Sulfides. Synlett 2018, 29, 336–339. DOI: 10.1055/s-0036-1591492.
  • Wang, D.; Zhang, R.; Lin, S.; Yan, Z.; Guo, S. Tetrabutylammonium Iodide Mediated Synthesis of β-Alkoxy Sulfides and Vinyl Sulfones by Using Benzenesulfonyl Chlorides as the Sulfur Sources under Acidic or Alkaline Conditions. Synlett 2016, 27, 2003–2008. DOI: 10.1055/s-0035-1561667.
  • Wang, D.; Zhang, R.; Ning, W.; Yan, Z.; Lin, S. Three-Component Oxysulfenylation Reaction: Two Simple and Convenient Approaches to β-Alkoxy Sulfides. Org. Biomol. Chem. 2016, 14, 5136–5140. DOI: 10.1039/C6OB00646A.
  • Yang, F.; Wang, F.; Wang, T.; Wang, Y.; Tian, S. Iodine-Catalyzed Three-Component Oxysulfenylation of Alkenes with Sulfonyl Hydrazides and Alcohols. Chem. Commun. 2014, 50, 2111–2113. DOI: 10.1039/c3cc48961b.
  • Gao, Y.; Gao, Y.; Tang, X.; Peng, J.; Hu, M.; Wu, W.; Jiang, H. Copper-Catalyzed Oxysulfenylation of Enolates with Sodium Sulfinates: A Strategy to Construct Sulfenylated Cyclic Ethers. Org. Lett. 2016, 18, 1158–1161. DOI: 10.1021/acs.orglett.6b00272.
  • Yu, J.; Gao, C.; Song, Z.; Yang, H.; Fu, H. Metal-Free Oxysulfenylation of Alkenes with 1-(Arylthio)pyrrolidine-2,5-Diones and Alcohols. Org. Biomol. Chem. 2015, 13, 4846–4850. DOI: 10.1039/c5ob00252d.
  • Guan, H.; Wang, H.; Huang, D.; Shi, Y. Enantioselective Oxysulfenylation and Oxyselenenylation of Olefins Catalyzed by Chiral Bronsted Acids. Tetrahedron 2012, 68, 2728–2735. DOI: 10.1016/j.tet.2012.01.006.
  • Denmark, S. E.; Kornfilt, D. J. P.; Vogler, T. Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes. J. Am. Chem. Soc. 2011, 133, 15308–15311. DOI: 10.1021/ja2064395.
  • Muangkaew, C.; Katrun, P.; Kanchanarugee, P.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetch, T.; Kuhakarn, C. PhI(OAc)2/KI Mediated 1,2-Acetoxysulfenylation of Alkenes: Facile Synthesis of Beta-Acetoxysulfiedes. Tetrahedron 2013, 69, 8847–8856. DOI: 10.1016/j.tet.2013.08.018.
  • Movassagh, B.; Navidi, M. One-Pot Synthesis of β-Hydroxysulfides from Styrenes and Disulfides Using the Zn/AlCl3 System. Tetrahedron Lett. 2008, 49, 6712–6714. DOI: 10.1016/j.tetlet.2008.09.071.
  • Taniguchi, N. Copper-Catalyzed 1,2-Hydroxysulfenylation of Alkene Using Disulfide via Cleavage of the S-S bond. J. Org. Chem. 2006, 71, 7874–7876. DOI: 10.1021/jo060834l.
  • Gao, X.; Pan, X.; Gao, J.; Jiang, H.; Yuan, G.; Li, Y. NH4I-Mediated Three-Component Coupling Reaction: Metal-Free Synthesis of beta-Alkoxy Methyl Sulfides from DMSO, Alcohols, and Styrenes. Org. Lett. 2015, 17, 1038–1041. DOI: 10.1021/acs.orglett.5b00170.
  • Yuan, Y.; Chen, Y.; Tang, S.; Huang, Z.; Lei, A. Electrochemical Oxidative Oxysulfenylation and Aminosulfenylation of Alkenes with Hydrogen Evolution. Sci. Adv. 2018, 4, eaat5312. DOI: 10.1126/sciadv.aat5312.
  • Zhang, T.; Dai, Y.; Cheng, S.; Liu, Y.; Yang, S.; Sun, B.; Tian, H. A Facile Method for the Sulfenyllactonization of Alkenoic Acids Using Dimethyl Sulfoxide Activated by Oxalyl Chloride. Synthesis 2017, 49, 1380–1386. DOI: 10.1055/s-0036-1588378.
  • Ding, R.; Lan, L.; Li, S.; Liu, Y.; Yang, S.; Tian, H.; Sun, B. A Novel Method of Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride. Synthesis 2018, 50, 2555–2566. DOI: 10.1055/s-0037-1609687.
  • Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H. Synthesis of Butenolides by Reactions of 3-Alkenoic Acids with Diphenyl Sulfoxide/Oxalyl Chloride. Flavour Fragr. J. 2018, 33, 397–404. DOI: 10.1002/ffj.3464.
  • Ding, R.; Li, J.; Jiao, W.; Han, M.; Liu, Y.; Tian, H.; Sun, B. A Highly Efficient Method for the Bromination of Alkenes, Alkynes and Ketones Using Dimethyl Sulfoxide and Oxalyl Bromide. Synthesis 2018, 50, 4325–4335. DOI: 10.1055/s-0037-1609560.
  • Lan, L.; Gao, Y.; Ding, R.; Zhang, T.; Liu, Y.; Sun, B.; Tian, H. A Facile Sulfenylchlorination of Alkenes with Me2SO/(COCl)2. Synth. Commun 2019, 49, 539–549. DOI: 10.1080/00397911.2018.1560473.
  • Gao, Y.; Cheng, S.; Zhang, T.; Ding, R.; Liu, Y.; Sun, B.; Tian, H. Dimethyl Sulfoxide/Oxalyl Chloride: A Useful Reagent for Sulfenyletherification. Synth. Commun. 2018, 48, 2773–2781. DOI: 10.1080/00397911.2018.1524495.

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