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Deoxygenation of sulfoxides with boron bromide reagents

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    Deoxygenation of sulfoxides with boron bromide reagents
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1984, 49, 23, 4538–4540
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    https://doi.org/10.1021/jo00197a043
    Published November 1, 1984
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    This article is cited by 46 publications.

    1. Ana C. Fernandes, José A. Fernandes, Carlos C. Romão, Luis F. Veiros, and Maria José Calhorda . Highly Efficient Reduction of Sulfoxides with the System Borane/Oxo-rhenium Complexes. Organometallics 2010, 29 (21) , 5517-5525. https://doi.org/10.1021/om100450a
    2. Kamil Mamleev, Václav Eigner, Hana Dvořáková, Pavel Lhoták. The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide. Molecules 2023, 28 (9) , 3914. https://doi.org/10.3390/molecules28093914
    3. Jianqiang Wang, Fangmin Shi, Dongyan Dai, Liping Xiong, Yongpo Yang. N -bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides. Phosphorus, Sulfur, and Silicon and the Related Elements 2021, 196 (5) , 439-443. https://doi.org/10.1080/10426507.2020.1871348
    4. Xingyue Wang, Changlin Xu, Hongyu Guan, Mi Lin, Peng Huang. Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent. Chinese Journal of Organic Chemistry 2021, 41 (8) , 3330. https://doi.org/10.6023/cjoc202102004
    5. Paola Acosta‐Guzmán, Camilo Mahecha‐Mahecha, Diego Gamba‐Sánchez. Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides. Chemistry – A European Journal 2020, 26 (45) , 10348-10354. https://doi.org/10.1002/chem.202001815
    6. Daniel M. Beagan, Veronica Carta, Kenneth G. Caulton. A reagent for heteroatom borylation, including iron mediated reductive deoxygenation of nitrate yielding a dinitrosyl complex. Dalton Transactions 2020, 49 (5) , 1681-1687. https://doi.org/10.1039/D0DT00077A
    7. Byung Woo Yoo, Jeeyeon Park, Hyo Jong Shin, Cheol Min Yoon. Rapid and efficient deoxygenation of sulfoxides to sulfides with tantalum(V) chloride/sodium iodide system. Journal of Sulfur Chemistry 2017, 38 (6) , 597-603. https://doi.org/10.1080/17415993.2017.1337770
    8. Guoqiang Wang, Honglin Zhang, Jiyang Zhao, Wei Li, Jia Cao, Chengjian Zhu, Shuhua Li. Homolytic Cleavage of a B−B Bond by the Cooperative Catalysis of Two Lewis Bases: Computational Design and Experimental Verification. Angewandte Chemie 2016, 128 (20) , 6089-6093. https://doi.org/10.1002/ange.201511917
    9. Guoqiang Wang, Honglin Zhang, Jiyang Zhao, Wei Li, Jia Cao, Chengjian Zhu, Shuhua Li. Homolytic Cleavage of a B−B Bond by the Cooperative Catalysis of Two Lewis Bases: Computational Design and Experimental Verification. Angewandte Chemie International Edition 2016, 55 (20) , 5985-5989. https://doi.org/10.1002/anie.201511917
    10. Byung Woo Yoo, Bo Ran Yu, Cheol Min Yoon. A facile and efficient procedure for the deoxygenation of sulfoxides to sulfides with the HfCl 4 /Zn system. Journal of Sulfur Chemistry 2015, 36 (4) , 358-363. https://doi.org/10.1080/17415993.2015.1031234
    11. Ramin Ghorbani-Vaghei, Lotfi Shiri, Arash Ghorbani-Choghamarani. A novel method for the reduction of sulfoxides with the N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide (TBBDA)/PPh3 system. Comptes Rendus Chimie 2014, 17 (10) , 1002-1006. https://doi.org/10.1016/j.crci.2013.11.006
    12. Kishor Padala, Masilamani Jeganmohan. Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aromatic sulfoxides with alkynes via C–H bond activation. Chem. Commun. 2014, 50 (93) , 14573-14576. https://doi.org/10.1039/C4CC06426G
    13. Stephan Enthaler. Zinc-Catalyzed Deoxygenation of Sulfoxides to Sulfides Applying [B(Pin)]2 as Deoxygenation Reagents. Catalysis Letters 2012, 142 (11) , 1306-1311. https://doi.org/10.1007/s10562-012-0897-y
    14. Stephan Enthaler, Sebastian Krackl, Elisabeth Irran, Shigeyoshi Inoue. Deoxygenation of Sulfoxides to Sulfides in the Presence of Zinc Catalysts and Boranes as Reducing Reagents. Catalysis Letters 2012, 142 (8) , 1003-1010. https://doi.org/10.1007/s10562-012-0862-9
    15. Stephan Enthaler, Maik Weidauer. Reduction of Sulfoxides to Sulfides in the Presence of Copper Catalysts. Catalysis Letters 2011, 141 (6) , 833-838. https://doi.org/10.1007/s10562-011-0590-6
    16. Dennis J. Milanowski, Jeff Keilman, Cheng Guo, Ulla Mocek. Isolation and identification of five impurities of ALB 109564(a) drug substance. Journal of Pharmaceutical and Biomedical Analysis 2011, 55 (2) , 366-372. https://doi.org/10.1016/j.jpba.2011.01.035
    17. Stephan Enthaler. A Facile and Efficient Iron‐Catalyzed Reduction of Sulfoxides to Sulfides. ChemCatChem 2011, 3 (4) , 666-670. https://doi.org/10.1002/cctc.201000400
    18. Stephan Enthaler. A straightforward zinc-catalysed reduction of sulfoxides to sulfides. Catalysis Science & Technology 2011, 1 (1) , 104. https://doi.org/10.1039/c0cy00039f
    19. Ivânia Cabrita, Sara C.A. Sousa, Ana C. Fernandes. Reduction of sulfoxides catalyzed by oxo-complexes. Tetrahedron Letters 2010, 51 (47) , 6132-6135. https://doi.org/10.1016/j.tetlet.2010.09.071
    20. Sara C.A. Sousa, Ana C. Fernandes. Highly efficient and chemoselective reduction of sulfoxides using the system silane/oxo-rhenium complexes. Tetrahedron Letters 2009, 50 (49) , 6872-6876. https://doi.org/10.1016/j.tetlet.2009.09.121
    21. Kyungsoo Oh, William Eric Knabe. Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn. Tetrahedron 2009, 65 (15) , 2966-2974. https://doi.org/10.1016/j.tet.2009.02.013
    22. John A. Soderquist, Qingwei Yao. 9-Bromo-9-borabicyclo[3.3.1]nonane. 2009https://doi.org/10.1002/047084289X.rb280.pub2
    23. Yvan Guindon, Paul C. Anderson, Qingwei Yao. Bromodimethylborane. 2009https://doi.org/10.1002/047084289X.rb289.pub2
    24. Habib Firouzabadi, Arezu Jamalian. Reduction of oxygenated organosulfur compounds. Journal of Sulfur Chemistry 2008, 29 (1) , 53-97. https://doi.org/10.1080/17415990701684776
    25. Ana C. Fernandes, Carlos C. Romão. Reduction of sulfoxides with boranes catalyzed by MoO2Cl2. Tetrahedron Letters 2007, 48 (52) , 9176-9179. https://doi.org/10.1016/j.tetlet.2007.10.106
    26. Kiumars Bahrami, Mohammad Mehdi Khodaei, Mohammad Khedri. A Novel Method for the Deoxygenation of Sulfoxides with the PPh3/Br2/CuBr System. Chemistry Letters 2007, 36 (11) , 1324-1325. https://doi.org/10.1246/cl.2007.1324
    27. Akira Suzuki, Shoji Hara, Xianhai Huang. Boron Tribromide. 2006https://doi.org/10.1002/047084289X.rb244.pub2
    28. Daniel J. Harrison, Nga Chiu Tam, Christopher M. Vogels, Richard F. Langler, R. Thomas Baker, Andreas Decken, Stephen A. Westcott. A gentle and efficient route for the deoxygenation of sulfoxides using catecholborane (HBcat; cat=1,2-O2C6H4). Tetrahedron Letters 2004, 45 (46) , 8493-8496. https://doi.org/10.1016/j.tetlet.2004.09.068
    29. Byung Woo Yoo, Kwang Hyun Choi, Sung Jae Lee, Cheol Min Yoon, Sung Hoon Kim, Joong Hyup Kim. MILD AND EFFICIENT REDUCTION OF SULFOXIDES TO SULFIDES WITH BIS -(CYCLOPENTADIENYL)TITANIUM(IV) DICHLORIDE–INDIUM SYSTEM. Synthetic Communications 2002, 32 (1) , 63-67. https://doi.org/10.1081/SCC-120001509
    30. Akira Suzuki, Shoji Hara. Boron Tribromide. 2001https://doi.org/10.1002/047084289X.rb244
    31. John A. Soderquist. 9-Bromo-9-borabicyclo[3.3.1]nonane. 2001https://doi.org/10.1002/047084289X.rb280
    32. Yvan Guindon, Paul C. Anderson. Bromodimethylborane. 2001https://doi.org/10.1002/047084289X.rb289
    33. Kazuhiro Kobayashi, Masataka Kawakita, Kouichi Yokota, Tohru Mannami, Koji Yamamoto, Osamu Morikawa, Hisatoshi Konishi. Reactions of Sulfoxides with Magnesium Amides. Transformation of Sulfoxides into Sulfides, Dithioacetals, and Vinyl Sulfides. Bulletin of the Chemical Society of Japan 1995, 68 (5) , 1401-1407. https://doi.org/10.1246/bcsj.68.1401
    34. Philip C. Bulman Page, Robin D. Wilkes, Dominic Reynolds. Alkyl Chalcogenides: Sulfur-based Functional Groups. 1995, 113-275. https://doi.org/10.1016/B0-08-044705-8/00156-4
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    37. Jean-Francois Lavallée, George Just. Asymmetric synthesis of 3′-carbomethoxymethyl 3′-deoxythymidine via radical cyclization. Tetrahedron Letters 1991, 32 (29) , 3469-3472. https://doi.org/10.1016/0040-4039(91)80808-J
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    40. Anton Meller. The System Boron-Bromine. 1988, 71-97. https://doi.org/10.1007/978-3-662-06138-1_2
    41. Michel Madesclaire. Reduction of sulfoxides to thioethers. Tetrahedron 1988, 44 (21) , 6537-6580. https://doi.org/10.1016/S0040-4020(01)90096-1
    42. B. Carboni, M. Vaultier, R. Carrié. Etude de la chimioselectivite de la reaction des dichloroboranes avec les azides fonctionnels : une synthese efficace d'amines secondaires fonctionnalisees.. Tetrahedron 1987, 43 (8) , 1799-1810. https://doi.org/10.1016/S0040-4020(01)81491-5
    43. Dallas K. Bates, Burnell A. Sell, Joseph A. Picard. An interrupted pummerer reaction induced by vilsmeier reagent (POCl3/DMF)1. Tetrahedron Letters 1987, 28 (31) , 3535-3538. https://doi.org/10.1016/S0040-4039(00)95528-X
    44. Yvan Guindon, Michael A Bernstein, Paul C Anderson. Ring cleavage of THP and THF ethers using dimethylboron bromide. Tetrahedron Letters 1987, 28 (20) , 2225-2228. https://doi.org/10.1016/S0040-4039(00)96086-6
    45. Y. GUINDON, J. G. ATKINSON, H. E. MORTON. ChemInform Abstract: DEOXYGENATION OF SULFOXIDES WITH BORON BROMIDE REAGENTS. Chemischer Informationsdienst 1985, 16 (16) https://doi.org/10.1002/chin.198516147
    46. Jin Soon Cha, Jin Euog Kim, Jong Dae Kim. Selective deoxygenation of sulfoxides with thexylchloroborane-methyl sulfide complex. Tetrahedron Letters 1985, 26 (52) , 6453-6456. https://doi.org/10.1016/S0040-4039(00)99025-7
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    Cite this: J. Org. Chem. 1984, 49, 23, 4538–4540
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo00197a043
    Published November 1, 1984
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