Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 9
216
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Convenient, Solvent-Free Method for Preparation of [Hydroxy(phosphoryloxy)iodo]arenes

, , &
Pages 1371-1376 | Received 12 Mar 2009, Published online: 07 Apr 2010

REFERENCES

  • (a) Varvoglis , A. Chemical transformations induced by hypervalent iodine reagents . Tetrahedron 1997 , 53 , 1179 ; (b) Stang , P. J. ; Zhdankin , V. V. Organic polyvalent iodine compounds . Chem. Rev. 1996 , 96 , 1123 ; (c) Zhdankin , V. V. ; Stang , P. J. Recent developments in the chemistry of polyvalent iodine compounds . Chem. Rev. 2002 , 102 , 2523 ; (d) Wirth , T. ; Hirt , U. H. Hypervalent iodine compounds: Recent advances in synthetic applications . Synthesis 1999 , 1271 ; (e) Kirschning , A. Hypervalent iodine and carbohydrates—A new liaison . Eur. J. Org. Chem. 1998 , 11 , 2267 ; (f) Ochiai , M. Nucleophilic vinylic substitutions of λ 3-vinyliodanes . J. Organomet. Chem. 2000 , 611 , 494 ; (g) Okuyama , T. Solvolysis of vinyl iodonium salts: New insights into vinyl cation intermediates . Acc. Chem. Res. 2002 , 35 , 12 ; (h) Zhdankin , V. V. ; Stang , P. J. Alkynyliodonium salts in organic synthesis . Tetrahedron 1998 , 54 , 10927 .
  • (a) Koser , G. F. ; Relenyi , A. G. ; Kalos , A. N. ; Rebrovic , L. ; Wettach , R. H. One-step α-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene. J. Org. Chem. 1982, 47, 2487; (b) Rebrovic , L. ; Koser , G. F. Reactions of alkenes with [hydroxy(tosyloxy)iodo]benzene: Stereospecific syn-1,2-ditosyloxylation of the carbon–carbon double bond and other processes. J. Org. Chem. 1984, 49, 2462; (c) Shah , M. ; Taschner , M. J. ; Koser , G. F. ; Rach , N. L. Tosyloxylactonization of alkenoic acids with [hydroxy(tosyloxy)iodo]benzene. Tetrahedron Lett. 1986, 27, 4557.
  • (a) Rebrovic , L. ; Koser , G. F. Alkynylaryliodonium tosylates and aryl[β-(tosyloxy)vinyl]iodonium tosylates from reactions of terminal alkynes with [hydroxy(tosyloxy)iodo]benzene . J. Org. Chem. 1984 , 49 , 4700 ; (b) Margida , A. J. ; Koser , G. F. Exchange of carbon ligands at iodine in iodonium salts: A direct synthesis of aryl(2-furyl)iodonium tosylates from aryl(tert-butylethynyl)iodonium tosylates . J. Org. Chem. 1984 , 49 , 4703 ; (c) Lodaya , J. S. ; Koser , G. F. Alkynyliodonium salts as alkynylating reagents: Direct conversion of alkynylphenyliodonium tosylates to dialkyl alkynylphosphonates with trialkyl phosphates . J. Org. Chem. 1990 , 55 , 1513 ; (d) Stang , P. J. ; Surber , B. M. Alkynyl sulfonate esters. Preparation and characterization of acetylenic tosylates, RC[tbnd]COTs . J. Am. Chem. Soc. 1985 , 107 , 1452 ; (e) Carman , C. S. ; Koser , G. F. Regiospecific synthesis of aryl(2-furyl)iodonium tosylates, a new class of iodonium salts, from [hydroxy(tosyloxy)iodo]arenes and 2-(trimethylsilyl)furans in organic solvents . J. Org. Chem. 1983 , 48 , 2534 ; (f) Margida , A. J. ; Koser , G. F. Direct condensation of [hydroxy(tosyloxy)iodo]arenes with thiophenes: A convenient, mild synthesis of aryl(2-thienyl)iodonium tosylates . J. Org. Chem. 1984 , 49 , 3643 .
  • Yusubov , M. S. ; Wirth , T. Solvent-free reactions with hypervalent iodine reagents . Org. Lett. 2005 , 7 , 519 .
  • Koser , G. F. ; Lodaya , J. S. ; Ray , D. G. III ; Kokil , P. B. Direct α-phosphoryloxylation of ketones and (phosphoryloxy)lactonization of pentenoic acids with [hydroxy[(bis(phenyloxy)phosphoryl)oxy]iodo]benzene . J. Am. Chem. Soc. 1988 , 110 , 2987 .
  • (a) Koser , G. F. ; Chen , X. ; Chen , K. ; Sun , G. Regiospecific conversion of terminal alkynes to ketol phosphates with an iodine (III)-phosphate reagent . Tetrahedron Lett. 1993 , 34 , 779 ; (b) Stang , P. J. ; Kitamura , T. ; Boehshar , M. ; Wingert , H. Acetylenic esters: Preparation and characterization of alkynyl dialkyl phosphates, RC.tplbond.COPO(OR′)2 . J. Am. Chem. Soc. 1989 , 111 , 2225 ; (c) Stang , P. J. ; Surber , B. M. ; Chen , Z.-C. ; Roberts , K. A. ; Anderson , A. G. Acetylenic esters: Preparation and mechanism of formation of alkynyl tosylates and mesylates via tricoordinate iodonium species . J. Am. Chem. Soc. 1987 , 109 , 228 .
  • (a) Welsh , C. Enzymatic Reaction Mechanisms ; W. H. Freeman Co. : San Francisco , 1979 ; (b) Grandour , R. D. ; Schowen , R. L. (Eds.). Transition States of Biochemical Processes ; Plenum Press : New York , 1978 ; (c) Metzler , D. Biochemistry: The Chemical Reactions of Living Cells ; Academic Press : New York , 1977 ; (d) Lehninger , A. Biochemistry, , 2nd ed. ; Worth : New York , 1975 .
  • Damle , S. V. , Seomoon , D. ; Lee , P. H. Palladium-catalyzed homocoupling reaction of 1-iodoalkynes: A simple and efficient synthesis of symmetrical 1,3-diynes . J. Org. Chem. 2003 , 68 , 7085 .
  • McKillop , A. ; Kemp , D. Further functional group oxidations using sodium perborate. Tetrahedron 1989, 45, 3299.
  • Loudon , G. M. ; Radhakrishna , A. S. ; Almond , M. R. Conversion of aliphatic amides into amines with [I,I-bis(trifluoroacetoxy)iodo]benzene, 1: Scope of the reaction . J. Org. Chem. 1984 , 49 , 4272 .
  • Saltzman , H. ; Sharefkin , J. Org. Synth. Collect. 1973 , 5 , 658 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.