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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 15
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Articles

Dichlorination of olefins with diphenyl sulfoxide/oxalyl chloride

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Pages 2319-2330 | Received 03 Dec 2019, Published online: 05 Jun 2020

References

  • Morella, A. M.; Ward, A. D. The Cis Chlorination of Alkenes Using Selenium Reagents. Tetrahedron Lett. 1984, 25, 1197–1200. DOI: 10.1016/S0040-4039(01)91559-X.
  • Sket, B.; Zupan, M.; Zupet, P. Role of the Polymer Backbone on the Reactivity of Polymer-Supported (Dichloroiodo) Benzene. Tetrahedron 1984, 40, 1603–1606. DOI: 10.1016/S0040-4020(01)91811-3.
  • (a) Markó, I. E.; Richardson, P. F. Controlling the Reactivity of Permanganate Anion. Novel, Stereospecific, Dichlorination of Olefins. Tetrahedron Lett. 1991, 32, 1831–1834. DOI: 10.1016/S0040-4039(00)74342-5. (b) Richardson, P. F.; Markó, I. E. On the Permanganate-Mediated Dichlorination of Olefins. Synlett 1991, 1991, 733–766. DOI: 10.1055/s-1991-20857. (c) Markó, I. E.; Richardson, P. F.; Bailey, M.; Maguire, A. R.; Coughlan, N. Selective Manganese-Mediated Transformations Using the Combination: KMnO4/Me3SiCl. Tetrahedron Lett. 1997, 38, 2339–2342. DOI: 10.1016/S0040-4039(97)00309-2. (d) Yakabe, S.; Hirano, M.; Morimoto, T. vic-Dichlorination of Olefins with Sodium Chlorite, Mn(Acac)3, and Moist Alumina in Dichloromethane. Synth. Commun. 1998, 28, 1871–1878. DOI: 10.1080/00397919808007018. (e) Hazra, B. G.; Chordia, M. D.; Basu, S.; Bahule, B. B.; Pore, V. S.; Naskar, D. Manganese-Mediated Stereoselective and Chemoselective Trans-Dichlorination of Alkenes with Tetradecyltrimethylammonium Permanganate-Trimethylchlorosilane. J. Chem. Res. 1998, 1998, 8–9. DOI: 10.1039/a700726d. (f) Hojo, M.; Murakami, C.; Ohno, K.; Kuboyama, J.; Nakamura, S.; Ito, H.; Hosomi, A. Di-Functionalization of Alkenes Using an Oxidant Generated from Manganese(II) Chloride under Oxygen: synthesis of γ-Lactones. Heterocycles 1998, 47, 97–100. DOI: 10.3987/COM-97-S(N)30.
  • Schlama, T.; Gabriel, K.; Gouverneur, V.; Mioskowski, C. Tetraethylammonium Trichloride: A Versatile Reagent for Chlorinations and Oxidations. Angew. Chem. Int. Ed. Engl. 1997, 36, 2342–2344. DOI: 10.1002/anie.199723421.
  • Barhate, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. V. Simple and Practical Halogenation of Arenes, Alkenes and Alkynes with Hydrohalic Acid/H2O2 (or TBHP). Tetrahedron 1999, 55, 11127–11142. DOI: 10.1016/S0040-4020(99)00628-6.
  • Sakai, K.; Sugimoto, K.; Shigeizumi, S.; Kondo, K. A New Selective Dichlorination of C-C Double Bonds. Tetrahedron Lett. 1994, 35, 737–740. DOI: 10.1016/S0040-4039(00)75804-7.
  • Ho, M. L.; Flynn, A. B.; Ogilvie, W. W. Single-Isomer Iodochlorination of Alkynes and Chlorination of Alkenes Using Tetrabutylammonium Iodide and Dichloroethane. J. Org. Chem. 2007, 72, 977–983. DOI: 10.1021/jo062188w.
  • Mendonca, G.; Mattos, M. Green Chlorination of Organic Compounds Using Trichloroisocyanuric Acid (TCCA). Cos 2014, 10, 820–836. DOI: 10.2174/157017941006140206102255.
  • Kamada, Y.; Kitamura, Y.; Tanaka, T.; Yoshimitsu, T. Dichlorination of Olefins with NCS/Ph(3)P. Org. Biomol. Chem. 2013, 11, 1598–1601. DOI: 10.1039/c3ob27345h.
  • (a) Ren, J.; Tong, R. Convenient in Situ Generation of Various Dechlorinating Agents from Oxone and Chloride: diastereoselective Dichlorination of Allylic and Homoallylic Alcohol Derivatives. Org. Biomol. Chem. 2013, 11, 4312–4315. DOI: 10.1039/c3ob40670a. (b) Stodulski, M.; Goetzinger, A.; Kohlhepp, S. V.; Gulder, T. Halocarbocyclization versus Dihalogenation: substituent Directed Iodine(III) Catalyzed Halogenations. Chem. Commun. (Camb) 2014, 50, 3435–3438. DOI: 10.1039/C3CC49850F. (c) Swamy, P.; Reddy, M.; Kumar, M.; Naresh, M.; Narender, N. N. Vicinal Dichlorination of Olefins Using NH4Cl and Oxone. ®. Synthesis 2013, 46, 251–257. DOI: 10.1055/s-0033-1340298.
  • Zeng, X.; Gong, C.; Zhang, J.; Xie, J. A Simple and Highly Diasteroselective Approach for the Vicinal Dichlorination of Functional Olefins. RSC Adv. 2016, 6, 85182–85185. DOI: 10.1039/C6RA20101F.
  • Ngatimin, M.; Gartshore, C. J.; Kindler, J. P.; Naidu, S.; Lupton, D. W. The α-Halogenation of α,β-Unsaturated Carbonyls and Dehalogenation of Alkenes Using Bisacetoxyiodobenzene/Pyridine Hydrohalides. Tetrahedron Lett. 2009, 50, 6008–6011. DOI: 10.1016/j.tetlet.2009.08.038.
  • (a) McCall, A. S.; Wang, H.; Desper, J. M.; Kraft, S. Bis-N-Heterocyclic Carbene Palladium(IV) Tetrachloride Complexes: synthesis, Reactivity, and Mechanisms of Direct Chlorinations and Oxidations of Organic Substrates. J. Am. Chem. Soc. 2011, 133, 1832–1848. DOI: 10.1021/ja107342b. (b) Moriuchi, T.; Fukui, Y.; Kato, S.; Kajikawa, T.; Hirao, T. Vanadium-Catalyzed Chlorination under Molecular Oxylgen. J. Inorg. Biochem. 2015, 147, 177–180. DOI: 10.1016/j.jinorgbio.2015.01.015.
  • Egami, H.; Yoneda, T.; Uku, M.; Ide, T.; Kawato, Y.; Hamashima, Y. Difunctionalization of Alkenes Using 1-Chloro-1,2-Benziodoxol-3-(1H)-One. J. Org. Chem. 2016, 81, 4020–4030. DOI: 10.1021/acs.joc.6b00295.
  • (a) Fu, N.; Sauer, G. S.; Lin, S. Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources. J. Am. Chem. Soc. 2017, 139, 15548–15553. DOI: 10.1021/jacs.7b09388. (b) Sauer, G. S.; Lin, S. An Electrocatalytic Approach to the Radical Difunctionalization of Alkenes. ACS Catal. 2018, 8, 5175–5187. DOI: 10.1021/acscatal.8b01069.
  • (a) Yoshimitsu, T.; Fukumoto, N.; Nakatani, R.; Kojima, N.; Tanaka, T. Asymmetric Total Synthesis of (+)-Hexachlorosulfolipid, a Cytotoxin Isolated from Adriatic Mussels. J. Org. Chem. 2010, 75, 5425–5437. DOI: 10.1021/jo100534d. (b) Nilewski, C.; Geisser, R. W.; Carreira, E. M. Total Synthesis of a Chlorosulpholipid Cytotoxin Associated with Seafood Poisoning. Nature 2009, 457, 573–576. DOI: 10.1038/nature07734. (c) Bedke, D. K.; Shibuya, G. M.; Pereira, A. R.; Gerwick, W. H.; Vanderwal, C. D. A Concise Enantioselective Synthesis of the Chlorosulfolipid Malhamensilipin A. J. Am. Chem. Soc. 2010, 132, 2542–2543. DOI: 10.1021/ja910809c.
  • (a) Gilbert, B. B.; Eey, S. T.-C.; Ryabchuk, P.; Garry, O.; Denmark, S. E. Organoselenium-Catalyzed Enantioselective Syn-Dichlorination of Unbiased Alkenes. Tetrahedron 2019, 75, 4086–4098. DOI: 10.1016/j.tet.2019.05.054. (b) Wedek, V.; van Lommel, R.; Daniliuc, C. G.; de Proft, F.; Hennecke, U. Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes. Angew. Chem. Int. Ed. Engl. 2019, 58, 9239–9243. DOI: 10.1002/anie.201901777. (c) Monaco, M. R.; Bella, M. A Formidable Challenge: Catalytic Asymmetric Dichlorination. Angew. Chem. Int. Ed. Engl. 2011, 50, 11044–11046. DOI: 10.1002/anie.201104843. (d) Nicolaou, K. C.; Simmons, N. L.; Ying, Y.; Heretsch, P. M.; Chen, J. S. Enantioselective Dichlorination of Allylic Alcohols. J. Am. Chem. Soc. 2011, 133, 8134–8137. DOI: 10.1021/ja202555m. (e) Cresswell, A. J.; Eey, S. T.-C.; Denmark, S. E. Catalytic, Stereoselective Dihalogenation of Alkenes: challenges and Opportunities. Angew. Chem. Int. Ed. Engl. 2015, 54, 15642–15682. DOI: 10.1002/anie.201507152. (f) Atwood, B. R.; Vanderwal, C. D. Catalytic Control of Chlorination. Nature Chem. 2015, 7, 99–100. DOI: 10.1038/nchem.2163. (g) Cresswell, A. J.; Eey, S. T.-C.; Denmark, S. E. Catalytic, Stereospecific Syn-Dichlorination of Alkenes. Nature Chem. 2015, 7, 146–152. DOI: 10.1038/nchem.2141.
  • 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 2016, 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 for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride. Synthesis 2018, 50, 2555–2566. DOI: 10.1055/s-0037-1609687.
  • Furukawa, N.; Inoue, T.; Aida, T.; Oae, S. Preparation of Alkyl Bromides from the Corresponding Alcohols and Me2SBr2. J. Chem. Soc. Chem. Commun. 1973, 1973, 212.
  • Corey, E. J.; Kim, C. U.; Takeda, M. A Method for Selective Conversion of Allylic and Benzylic Alcohols to Halides under Neutral Conditions. Tetrahedron Lett. 1972, 13, 4339–4342. DOI: 10.1016/S0040-4039(01)94310-2.
  • 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.
  • Ding, R.; Li, J.; Jiao, W.; Han, M.; Liu, Y.; Tian, H.; Sun, B. A Highly Efficient Method for Bromination of Alkenes, Alkynes, and Ketones Using Dimethyl Sulfoxide and Oxalyl Bromide. Synthesis 2018, 50, 4325–4335. DOI: 10.1055/s-0037-1609560.

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