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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 1
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Original Articles

Mild and Efficient Reduction of Sulfoxides to Sulfides with Titanium Tetrachloride–Indium System

Byung Woo Yoo Department of Chemistry, Korea University, Jochiwon, Chungnam, Korea; Department of Chemistry, Korea University, Jochiwon, Chungnam, 339-700, KoreaCorrespondencebwyoo@ korea.ac.kr
,
Kwang Hyun Choi Department of Chemistry, Korea University, Jochiwon, Chungnam, Korea
,
Dong Yoon Kim Department of Chemistry, Korea University, Jochiwon, Chungnam, Korea
,
Kyung Il Choi Biochemicals Research Center, Korea Institute of Science and Technology, Cheongryang, Seoul, Korea
&
Joong Hyup Kim Biochemicals Research Center, Korea Institute of Science and Technology, Cheongryang, Seoul, Korea
Pages 53-57 | Received 15 Oct 2001, Published online: 29 Jun 2011

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Byung Woo Yoo, Hyung Min Kim & Duckil Kim. (2013) Selective and Efficient Deoxygenation of Sulfoxides with NbCl5/Indium System. Synthetic Communications 43:15, pages 2057-2061.
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Seied Ali Pourmousavi & Parvin Salehi. (2010) A Simple and Efficient Method for Reduction of Sulfoxide Under Solvent-Free Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 185:4, pages 803-807.
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Habib Firouzabadi & Arezu Jamalian. (2008) Reduction of oxygenated organosulfur compounds. Journal of Sulfur Chemistry 29:1, pages 53-97.
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Byung Woo Yoo, Min Chol Park & Min Suk Song. (2007) Mild and Efficient Deoxygenation of Sulfoxides with a WCl6/Indium System. Synthetic Communications 37:22, pages 4079-4083.
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Byung Woo Yoo, Min Suk Song & Min Chol Park. (2007) Mild and Efficient Deoxygenation of Sulfoxides with MoCl5/Indium System. Synthetic Communications 37:18, pages 3089-3093.
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Jung Hwa Han, Kyung Il Choi, Joong Hyup Kim, Cheol Min Yoon & Byung Woo Yoo. (2006) Facile Deoxygenation of Amine‐N‐oxides With CoCl2 · 6H2O–Indium System. Synthetic Communications 36:4, pages 415-419.
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H. Firouzabadi, N. Iranpoor & M. Jafarpour. (2005) ZrCl4/NaI and ZrOCl2 · 8H2O/NaI as effective systems for reductive coupling of sulfonyl chlorides and chemoselective deoxygenation of sulfoxides. Journal of Sulfur Chemistry 26:4-5, pages 313-324.
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Byung Woo Yoo, Kwang Hyun Choi, Kyung Il Choi & Joong Hyup Kim. (2003) Mild and Efficient Deoxygenation of Amine-N-oxides with Titanium Tetrachloride-Indium System. Synthetic Communications 33:24, pages 4185-4189.
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Articles from other publishers (34)

Anthony Bongso, Robby Roswanda & Yana Maolana Syah. (2022) Recent advances of carbonyl olefination via McMurry coupling reaction . RSC Advances 12:25, pages 15885-15909.
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Aimee K. ClarkeAlison Parkin, Richard J. K. TaylorWilliam P. Unsworth & James A. Rossi-Ashton. (2020) Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications. ACS Catalysis 10:10, pages 5814-5820.
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Maria S. Ledovskaya, Vladimir V. Voronin & Konstantin S. Rodygin. (2018) Methods for the synthesis of O-, S- and N-vinyl derivatives. Russian Chemical Reviews 87:2, pages 167-191.
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Xia Zhao, Xiancai Zheng, Bo Yang, Jianqiao Sheng & Kui Lu. (2018) Deoxygenation of sulphoxides to sulphides with trichlorophosphane. Organic & Biomolecular Chemistry 16:7, pages 1200-1204.
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Lotfi Shiri & Mosstafa Kazemi. (2017) Deoxygenation of sulfoxides. Research on Chemical Intermediates 43:11, pages 6007-6041.
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Hua-Jie Zhu. 2015. Organic Stereochemistry. Organic Stereochemistry 205 239 .
Hsiao Wei Chen, T. S. Andy Hor, Roberto Pattacini & Pierre Braunstein. (2015) Unexpected synthesis of an Au 2 In 2 tetrametallatricyclic complex from α-aminophosphines and formation of Au–In–P and Ag–In–P nanomaterials . Dalton Transactions 44:37, pages 16242-16246.
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Ramin Ghorbani-Vaghei, Lotfi Shiri & Arash Ghorbani-Choghamarani. (2014) A novel method for the reduction of sulfoxides with the N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide (TBBDA)/PPh3 system. Comptes Rendus Chimie 17:10, pages 1002-1006.
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A.-C. Gaumont, M. Gulea, S. Perrio & V. Reboul. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 535 563 .
Stephan Enthaler. (2012) Zinc-Catalyzed Deoxygenation of Sulfoxides to Sulfides Applying [B(Pin)]2 as Deoxygenation Reagents. Catalysis Letters 142:11, pages 1306-1311.
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Byung-Woo Yoo, Duck-Il Kim, Hyung-Min Kim & Sung-Ho Kang. (2012) Efficient and Selective Reduction of Aromatic Nitro Compounds to Aromatic Amines by NbCl 5 /Indium System . Bulletin of the Korean Chemical Society 33:9, pages 2851-2852.
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Sara C.A. Sousa, Joana R. Bernardo, Carlos C. Romão & Ana C. Fernandes. (2012) Highly efficient rhenium-catalyzed deoxygenation of sulfoxides without adding any reducing agent. Tetrahedron 68:39, pages 8194-8197.
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Stephan Enthaler, Sebastian Krackl, Elisabeth Irran & Shigeyoshi Inoue. (2012) Deoxygenation of Sulfoxides to Sulfides in the Presence of Zinc Catalysts and Boranes as Reducing Reagents. Catalysis Letters 142:8, pages 1003-1010.
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Mojtaba Bagherzadeh, Mohammad Mehdi Haghdoost, Mojtaba Amini & Parviz Gohari Derakhshandeh. (2012) Molybdenum oxo–peroxo complex: A very fast catalyst for oxidation and reduction of sulfur-based compounds. Catalysis Communications 23, pages 14-19.
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Kiumars Bahrami, Mohammad M. Khodaei & Samira Sohrabnezhad. (2011) Cyanuric chloride as promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Tetrahedron Letters 52:48, pages 6420-6423.
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Byung-Woo Yoo, Hyung-Min Kim, Duck-Il Kim & Kyoung-Sun Seok. (2011) Rapid and Efficient Deoxygenation of Sulfoxides with NbCl 5 /NaI System . Bulletin of the Korean Chemical Society 32:8, pages 2525-2526.
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Stephan Enthaler & Maik Weidauer. (2011) Reduction of Sulfoxides to Sulfides in the Presence of Copper Catalysts. Catalysis Letters 141:6, pages 833-838.
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Stephan Enthaler. (2011) A Facile and Efficient Iron‐Catalyzed Reduction of Sulfoxides to Sulfides. ChemCatChem 3:4, pages 666-670.
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Stephan Enthaler. (2011) A straightforward zinc-catalysed reduction of sulfoxides to sulfides. Catalysis Science & Technology 1:1, pages 104.
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Ana C. Fernandes, José A. Fernandes, Carlos C. Romão, Luis F. Veiros & Maria José Calhorda. (2010) Highly Efficient Reduction of Sulfoxides with the System Borane/Oxo-rhenium Complexes. Organometallics 29:21, pages 5517-5525.
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Ivânia Cabrita, Sara C.A. Sousa & Ana C. Fernandes. (2010) Reduction of sulfoxides catalyzed by oxo-complexes. Tetrahedron Letters 51:47, pages 6132-6135.
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Sara C.A. Sousa & Ana C. Fernandes. (2009) Highly efficient and chemoselective reduction of sulfoxides using the system silane/oxo-rhenium complexes. Tetrahedron Letters 50:49, pages 6872-6876.
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. (2009) Rapid and Mild Deoxygenation of Sulfoxides with MoCl 5 /Gallium System under Ultrasonication . Bulletin of the Korean Chemical Society 30:9, pages 1927-1928.
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Ottorino De Lucchi, Giulia Licini, Larissa B. Krasnova & Andrei K. Yudin. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Ana C. Fernandes & Carlos C. Romão. (2007) Reduction of sulfoxides with boranes catalyzed by MoO2Cl2. Tetrahedron Letters 48:52, pages 9176-9179.
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Kiumars Bahrami, Mohammad Mehdi Khodaei & Mohammad Khedri. (2007) A Novel Method for the Deoxygenation of Sulfoxides with the PPh 3 /Br 2 /CuBr System . Chemistry Letters 36:11, pages 1324-1325.
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Guoxiong Hua & J. Derek Woollins. (2007) The syntheses of sulfides by deoxygenation of sulfoxides using Woollins’ reagent. Tetrahedron Letters 48:21, pages 3677-3679.
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Ana C. Fernandes & Carlos C. Romão. (2006) A novel method for the reduction of sulfoxides and pyridine N-oxides with the system silane/MoO2Cl2. Tetrahedron 62:41, pages 9650-9654.
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. (2006) A Facile and Efficient Reduction of Nitroarenes with NiCl2？H2O/Indium System. Bulletin of the Korean Chemical Society 27:8, pages 1115-1116.
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. (2005) A Facile Deoxygenation of Amine-N-oxides with NiCl 2 .6H 2 O/Indium System . Bulletin of the Korean Chemical Society 26:12, pages 1921-1922.
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Tobias Wedel & Joachim Podlech. (2005) Enolate Addition to a 2-Alkylidene[1,3]dithiane-Derived Bissulfoxide. A New a 2 -Acceptor . Organic Letters 7:18, pages 4013-4015.
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Satoshi Kikuchi, Hiroyuki Konishi & Yukihiko Hashimoto. (2005) The deoxygenation of sulfoxide mediated by the Ph3P/Lewis acid combination and the application to the kinetic resolution of racemic phosphines using optically active sulfoxide. Tetrahedron 61:14, pages 3587-3591.
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Gurpreet S. Bhatia & Piotr P. Graczyk. (2004) A mild protocol for the deoxygenation of α-hydrogen-containing sulfoxides to the corresponding sulfides. Tetrahedron Letters 45:27, pages 5193-5195.
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Byung Woo Yoo, Kwang Hyun Choi, Dong Yoon Kim, Kyung Il Choi & Joong Hyup Kim. (2003) Mild and Efficient Reduction of Sulfoxides to Sulfides with Titanium Tetrachloride—Indium System.. ChemInform 34:22.
Crossref

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