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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 14
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Original Articles

Simple and Convenient Method for the Synthesis of Aryltellurophosphates Catalyzed by Cesium Hydroxide

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Pages 2088-2093 | Received 19 Oct 2013, Published online: 09 Jun 2014

REFERENCES

  • Eckstein , F. ; Gish , G. Phosphorothioates in molecular biology . Trends Biochem. Sci. 1989 , 14 , 97 – 100 .
  • Vyle , J. S. ; Li , X. ; Cosstick , R. New methods for the synthesis of 3′-S-phosphorothiolate internucleoside linkages . Tetrahedron Lett. 1992 , 33 , 3071 – 3075 .
  • Gao , Y. X. ; Guo , T. ; Cao , Y. ; Zhao , Y. F. A novel and general method for the formation of S-aryl, Se-aryl, and Te-aryl phosphorochalcogenoates . Synthesis 2009 , 7 , 1081 – 1086 .
  • Han , L. B. ; Choi , N. ; Tanaka , M. Facile oxidative addition of the phosphorous-selenium bond to Pd(0) and Pt(0) complexes and development of Pd-catalyzed regio- and stereoselective selenophosphorylation of alkynes . J. Am. Chem. Soc. 1996 , 118 , 7000 – 7001 .
  • Lopin , C. ; Gouhier , G. ; Gautier , A. ; Piettre , S. R. Phosphonyl, phosphonothioyl, phosphonodithioyl, and phosphonotrithioyl radicals: generation and study of their addition onto alkenes . J. Org. Chem. 2003 , 68 , 9916 – 9923 .
  • Fukuoka , M. ; Shuto , S. ; Minakawa , N. ; Ueno , Y. ; Matsuda , A. Alternative synthesis of cyclic IDP-carbocyclic ribose: Efficient cyclization of an 8-bromo-Nl-[5-(phosphoryl)- carbocyclic-ribosyl]inosine 5′-phenylthiophosphate derivative mediated by iodine . Tetrahedron Lett. 1999 , 40 , 5361 – 5364 .
  • Marinozzi , M. ; Fulco , M. C. ; Rizzo , R. ; Pellicciari , R. Synthesis of novel unsymmetrically bridgehead-substituted phenylselenobicyclo [1.1.1] pentanes . Synlett 2004 , 1027 – 1028 .
  • Glass , R. S. ; Singh , W. P. ; Jung , W. ; Veres , Z. ; Scholz , T. D. ; Stadtman , T. Monoselenophosphate: Synthesis, characterization, and identity with the prokaryotic biological selenium donor, compound SePX . Biochemistry 1993 , 32 , 12555 – 12559 .
  • Herpin , T. F. ; Motherwell , W. B. ; Roberts , B. P. ; Roland , S. ; Weibel , J. M. Free radical chain reactions for the preparation of novel anomeric carbohydrate difluoromethylene -phosphonates and -phosphonothioates . Tetrahedron 1997 , 53 , 15085 – 15100 .
  • Watanabe , Y. ; Inoue , S. ; Yamamoto , T. ; Ozaki , S. Phosphorothioate synthesis based on the redox reaction of phosphite with tellurium(IV) chlooride . Synthesis 1995 , 1243 – 1244 .
  • Chen , D. J. ; Chen , Z. C. Hypervalent iodine in synthesis 51: A facile novel synthetic access to Se-phenyl O,O-dialkyl phosphoroselenoates . J. Chem. Res. 2000 , 370 – 371 .
  • Masson , S. ; Saint-Clair , J. F. ; Saquet , M. Two methods for synthesis of (2-mercapto- phenyl)phosphonic acid . Synthesis 1993 , 485 – 486 .
  • Matier , C. E. ; Roth , H. J. A new synthesis of thiophosphoric acid esters with a C-S-P bond . Tetrahedron Lett. 1990 , 131 , 501 – 502 .
  • Chen , D. J. ; Chen , Z. C. Hypervalent iodine in synthesis, 49: A new effective synthesis of Se-phenyl O,O-dialkyl phosphoroselenoates with polymer-supported phenyliodine diacetate . Synth. Commun. 2001 , 31 , 421 – 424 .
  • Liu , D. D. ; Chen , D. W. ; Chen , Z. C. Hypervalent iodine in synthesis, XII: A new and convenient method for preparation of O,O-dialkyl S-aryl phosphorothiolates . Synth. Commun. 1992 , 22 , 2903 – 2908 .
  • Xu , Q. ; Liang , C. G. ; Huang , X. Free radical reaction of dialkyl phosphites and organic dichalcogenides: A new facile and convenient preparation of arylselenoposphates . Synth. Commun. 2003 , 33 , 2777 – 2785 .
  • Chen , J. M. ; Huang , X. A facile preparation of organyltellurophosphates. Synth. Commun. 2004, 34, 1745–1752.
  • Chen , J. M. ; Lin , X. J. ; Huang , X. A convenient preparation of organyltellurophosphates using a polymer-supported hypervalent iodine(III) reagent . Chem. Res. 2004 , 43 – 44 .
  • Hayashi , M. ; Miura , T. ; Matsuchika , K. ; Watanabe , Y. A general method for the synthesis of Te-aryl phosphorotellurate triesters . Synthesis 2004 , 9 , 1481 – 1485 .
  • Clive , D. L. J. ; Menchen , S. M. Alkali metal O, O- diethyl phosphorotelluroates, a reagent class for deoxygenation of epoxides, especially terminal epoxides . J. Org. Chem. 1980 , 45 , 2347 – 2354 .
  • Zhang , Q. L. ; Zeng , J. C. ; Xu , X. H. ; Zhou , B. ; Lu , R. L. ; Chen , X. ; Li , Y. J. Synthesis and biologic activities of glycerothiophospholipid conjugate of tegafur containing aryl-selenium group in the glycerol skeleton . Chem. J. Chin. Univ. 2005 , 26 , 2046 – 2051 .
  • Xia , X. ; Zou , K. B. ; Li , R. X. ; Zhang , Z. Y. ; Shao , L. L. ; Fang , D. W. ; Xu , X. H. Study of cesium hydroxide–catalyzed reactions of diaryl disulfides and ditellurides with terminal acetylenes . Acta Chim. Sinica 2008 , 66 , 1749 – 1752 .
  • Xia , X. ; Li , J. P. ; Zou , K. B. ; Fang , D. W. ; Zhang , Z. Y. ; Xu , Y. L. ; Xu , X. H. Cesium hydroxide–promoted reaction of element selenium with terminal alkynes and diaryliodonium salts to synthesize acetylenic arylselenides . Chin. J. Org. Chem. 2009 , 29 , 112 – 114 .
  • Wallace , T. J. ; Schriesheim , A. ; Bartok , W. The base-catalyzed oxidation of mercaptans, III: Role of the solvent and effect of mercaptan structure on the rate determining step . J. Org. Chem. 1963 , 28 , 1311 – 1314 .
  • Karimi , B. ; Hazarkhani , H. ; Zareyee , D. Trimethylchlorosilane (TMSCl) and cyanuric chloride (CC)–catalyzed efficient oxidative coupling of thiols with dimethylsulfoxide . Synthesis 2002 , 17 , 2513 – 2516 .

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