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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 14
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Original Articles

Stereoselective Synthesis of (Z)-1,2-Diarylthio-1-alkene via the Reaction of Diaryl Disulfides with Terminal Alkynes Catalyzed by Cesium Hydroxide

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Pages 2464-2471 | Received 15 Sep 2008, Published online: 16 Jun 2009

REFERENCES

  • Beletskaya , I. ; Moberg , C. Element–element addition to alkynes catalyzed by the group 10 metals . Chem. Rev. 1999 , 99 , 3435 – 3462 .
  • Kondo , T. ; Mitsudo , T. Metal-catalyzed carbon–sulfur bond formation . Chem. Rev. 2000 , 100 , 3205 – 3220 .
  • Heiba , E. I. ; Dessau , R. M. Free-radical addition of organic disulfides to acetylenes . J. Org. Chem. 1967 , 32 , 3837 – 3840 .
  • Kuniyasu , H. ; Ogawa , A. ; Miyazaki , S. I. ; Ryu , I. ; Kambe , N. ; Sonoda , N. Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes . J. Am. Chem. Soc. 1991 , 113 , 9796 – 9803 .
  • Moro , A. V. ; Nogueira , C. W. ; Barbosa , N. B. V. ; Mendes , P. H. ; Rocha , J. B. T. ; Zeni , G. Highly stereoselective one-pot procedure to prepare unsymmetrical bis- and tris-chalcogenide alkenes via addition of disulfides and diselenides to terminal alkynes. J. Org. Chem. 2005, 70, 5257–5268.
  • Ananikov , V. P. ; Kabeshov , M. A. ; Beletskaya , I. P. Mechanistic study of palladium-catalyzed S-S and Se-Se bonds addition to alkynes . J. Organomet. Chem. 2003 , 687 , 451 – 461 .
  • Ananikov , V. P. ; Kabeshov , M. A. ; Beletskaya , I. P. The first example of polymer-supported palladium-catalyst for stereosective S-S bond addition to terminal alkynes . Synlett 2005 , 6 , 1015 – 1017 .
  • Ananikov , V. P. ; Beletskaya , I. P. Palladium-catalyzed addition of disulfides and diselenides to alkynes under solvent free conditions . Org. Biomol. Chem. 2004 , 2 , 284 – 287 .
  • Ananikov , V. P. ; Kabeshov , M. A. ; Beletskaya , I. P. ; Khrustalev , V. N. ; Antipin , M. Y. New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands . Organometallics 2005 , 24 , 1275 – 1283 .
  • Usugi , S. I. ; Yorimitsu , H. ; Shinokubo , H. ; Oshima , K. Disulfidation of alkynes and alkenes with gallium trichloride . Org. Lett. 2004 , 6 , 601 – 603 .
  • Benati , L. ; Montevecchi , P. C. ; Spagnolo , P. Free-radical reactions of benzenethiol and diphenyl disulphide with alkynes: Chemical reactivity of intermediate 2-(phenylthio)vinyl radicals . J. Chem. Soc., Perkin Trans. 1 1991 , 9 , 2103 – 2110 .
  • Ogawa , A. ; Ikeda , T. ; Kimura , K. ; Hirao , T. Highly regio- and stereocontrolled synthesis of vinyl sulfides via transition-metal-catalyzed hydrothiolation of alkynes with thiols . J. Am. Chem. Soc. 1999 , 121 , 5108 – 5114 .
  • Kondoh , A. ; Yorimitsu , H. ; Oshima , K. Palladium-catalyzed anti-hydrothiolation of 1-alkynylphosphines . Org. Lett. 2007 , 9 , 1383 – 1385 .
  • Manarin , F. ; Roehrs , J. A. ; Prigol , M. ; Alves , D. ; Nogueria , C. W. ; Zeni , G. Regio- and stereoselective synthesis of vinyl sulfides via PhSeBr-catalyzed hydrothiolation of alkynes . Tetrahedron Lett. 2007 , 48 , 4805 – 4808 .
  • Dabdoub , M. J. ; Guerrero , P. J. Jr. Hydroalumination of phenylthioacetylenes: Synthesis and reactions of (Z)- and (E)-1-butyltelluro-1-phenylthio-1-alkenes . Tetrahedron Lett. 2001 , 42 , 7167 – 7172 .
  • Watanabe , S. I. ; Mori , E. ; Nagai , H. ; Iwamura , T. ; Iwama , T. ; Kataoka , T. A novel stereoselective preparation of various vinyl sulfide derivatives using β-alkylthioalkenylselenonium salts . J. Org. Chem. 2000 , 65 , 8893 – 8898 .
  • Huang , X. ; Xu , X. H. ; Zheng , W. X. Stereoselective synthesis of (E)-vinylsulfides via the reaction of vinylzirconium compounds with disulfides . Synth. Commun. 1999 , 29 , 2399 – 2404 .
  • Tzalis , D. ; Knochel , P. Cesium hydroxide: A superior base for the catalytic alkynylation of aldehydes and ketones and catalytic alkenylation of nitriles . Angew. Chem. Int. Ed. 1999 , 38 , 1463 – 1465 .
  • Cohen , R. J. ; Fox , D. L. ; Salvatore , R. N. A novel and highly efficient synthetic route to unsymmetrical organoselenides using cesium bases. J. Org. Chem. 2004, 69, 4265–4268.
  • Zeng , J. C. ; Lu , R. L. ; Xu , X. H. Highly selective synthesis of (Z)-1,2-bis(arylseleno)-1alkenes via addition of diaryldiselenides to terminal acetylenes catalyzed by cesium hydroxide . Chin. J. Org. Chem. 2004 , 24 , 1482 – 1484 .
  • Zou , K. B. ; Qiu , R. H. ; Fang , D. W. ; Liu , X. Y. ; Xu , X. H. Cesium hydroxide-catalyzed reaction of terminal alkynes with diarylditellurides to synthesize alkynyl tellurides . Synth. Commun. 2008 , 38 ( 13 ), 2237 – 2242 .
  • Bieber , L. W. ; Silva , M. F. ; Menezes , P. H. Short and efficient preparation of alkynyl selenides, sufides, and tellurides from terminal alkynes . Tetrahedron Lett. 2004 , 45 , 2735 – 2737 .

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