Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 13
284
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Mild and Efficient Chemoselective Tetrahydropyranylation of Alcohols Using Brønsted Acidic Ionic Liquid as Catalyst Under Solvent-Free Conditions

&
Pages 1995-2006 | Received 06 Nov 2010, Published online: 26 Mar 2012

REFERENCES

  • (a) Green , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis; , 3rd ed. ; John Wiley : New York , 1999 , p. 306 ; (b) Caine , D. ; Deutsch , H. Total synthesis of (−)-axisonitrile-3: An application of the reductive ring opening of vinylcyclopropanes. J. Am. Chem. Soc. 1978, 100, 8031 ; (c) Isobe , M. ; Iio , H. ; Kawai , T. ; Goto , T. Synthesis of sesquiterpene antitumor lactones, 2: A new stereocontrolled total synthesis of (±)-vernolepin. J. Am. Chem. Soc. 1978, 100, 1942.
  • (a) Boom , J. H. V. ; Herschied , J. D. M. ; Reese , C. B. p-Toluenesulfonic acid as a catalyst for the rapid tetrahydropyranylation and methoxytetrahydropyranylation of steroidal alcohols . Synthesis 1973 , 167 ; (b) Miyashita , M. ; Yoshikoshi , A. ; Grieco , P. A. Pyridinium p-toluenesulfonate: A mild and efficient catalyst for the tetrahydropyranylation of alcohols . J. Org. Chem. 1977 , 42 , 3772 ; (c) Shimizu , K. ; Hayashi , E. ; Hatamachi , T. ; Kodama , T. ; Kitayama , Y. SO3H-functionalized silica for acetalization of carbonyl compounds with methanol and tetrahydropyranylation of alcohols . Tetrahedron Lett. 2004 , 45 , 5135 .
  • (a) Tamami , B. ; Parvanak , K. Chemoselective tetrahydropyranylation of alcohols and phenols using polystyrene supported aluminium chloride as a catalyst . Tetrahedron Lett. 2004 , 45 , 715 ; (b) Namboodiri , V. V. ; Varma , R. S. Solvent-free tetrahydropyranylation (THP) of alcohols and phenols and their regeneration by catalytic aluminum chloride hexahydrate . Tetrahedron Lett. 2002 , 43 , 1143 ; (c) Babu , B. S. ; Balasubramanian , K. Mild and efficient tetrahydropyranylation of alcohols—Catalysis by lithium perchlorate in diethyl ether . Tetrahedron Lett. 1998 , 39 , 9287 .
  • (a) Bongini , A. ; Cardillo , G. ; Orena , M. ; Sandri , S. A simple and practical method for tetrahydropyranylation of alcohols and phenols . Synthesis 1979 , 618 ; (b) Olah , G. A. ; Husain , A. ; Singh , B. P. Catalysis by solid superacids, 191: Simplified and improved polymeric perfluorinated resin aulfonic acid (Nafion-H)–catalyzed protection-deprotection . Synthesis 1983 , 892 .
  • Karimi , B. ; Maleki , J. Lithium triflate (LiOTf)–catalyzed efficient and chemoselective tetrahydropyranylation of alcohols and phenols under mild and neutral reaction conditions . Tetrahedron Lett. 2002 , 43 , 5353 .
  • Habibi , M. H. ; Tangestaninejad , S. ; Mohamadpoor , I. ; Mirkhani , V. ; Yadollahi , B. Potassium dodecatangestocobaltate trihydrate (K5CoW12O40 · 3H2O): A mild and efficient catalyst for the tetrahydropyranylation of alcohols and their detetrahydropyranylation . Tetrahedron Lett. 2001 , 42 , 2851 .
  • Khan , A. T. ; Choudhury , L. H. ; Ghosh , S. Cupric sulfate pentahydrate (CuSO4 · 5H2O): A mild and efficient catalyst for tetrahydropyranylation/depyranylation of alcohols and phenols . Tetrahedron Lett. 2004 , 45 , 7891 .
  • Mineno , T. A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate . Tetrahedron Lett. 2002 , 43 , 7975 .
  • Wang , Y. G. ; Wu , X. X. ; Jiang , Z. Y. A mild and efficient selective tetrahydropyranylation of primary alcohols and deprotection of THP ethers of phenols and alcohols using PdCl2(CH3CN)2 as catalyst . Tetrahedron Lett. 2004 , 45 , 2973 .
  • Ranu , B. C. ; Saha , M. A simple, efficient, and selective method for tetrahydropyranylation of alcohols on a solid phase of alumina impregnated with zinc chloride. J. Org. Chem. 1994, 59, 8269.
  • Deka , N. ; Sarma , J. C. Microwave-mediated selective monotetrahydropyranylation of symmetrical diols catalyzed by iodine . J. Org. Chem. 2001 , 66 , 1947 .
  • Ravindranath , N. ; Ramesh , C. ; Das , B. Simple, facile, and highly selective tetrahydropyranylation of alcohols using silica chloride . Synlett 2001 , 1777 .
  • Naik , S. ; Gopinath , R. ; Patel , B. K. Tetrabutylammoniumtribromide (TBATB)–promoted tetrahydropyranylation/depyranylation of alcohols . Tetrahedron Lett. 2001 , 42 .
  • Curini , M. ; Epifano , F. ; Marcotullio , M. C. ; Rosati , O. Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in tetrahydropyranylation of alcohols and phenols . Tetrahedron Lett. 1998 , 39 , 8159 .
  • Branco , L. C. ; Afonso , C. A. M. Ionic liquids as recyclable reaction media for the tetrahydropyranylation of alcohols . Tetrahedron 2001 , 57 , 4405 .
  • Kumar , P. ; Dinesh , C. U. ; Reddy , R. S. ; Pandey , B. H-Y zeolite: A mild and efficient catalyst for the tetrahydropyranylation of alcohols . Synthesis 1993 , 1069 .
  • Hoyer , S. ; Laszlo , P. ; Orlovic , M. ; Polla , E. Catalysis by acidic clay of the protective tetrahydropyranylation of alcohols and phenols . Synthesis 1986 , 655 .
  • Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 .
  • Cole , A. C. ; Jensen , J. L. ; Ntai , I. ; Tran , K. L. T. ; Weaver , K. J. ; Forbes , D. C. ; Davis Jr. , J. H. Novel Brønsted acidic ionic liquids and their use as dual solvent–catalysts . J. Am. Chem. Soc. 2002 , 124 , 5962 .
  • Kwan , J. ; Kim , M.-J. Ionic liquid–coated enzyme for biocatalysis in organic solvent . J. Org. Chem. 2002 , 67 , 6845 .
  • Luo , S. ; Mi , X. ; Zhang , L. ; Liu , S. ; Xu , H. ; Chenga , J. Functionalized ionic liquids catalyzed direct aldol reactions . Tetrahedron 2007 , 63 , 1923 .
  • Fraga-Dubreuil , J. ; Bourahla , K. ; Rahmouni , M. ; Bazureau , J. P. ; Hamelin , J. Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media . Catal. Commun. 2002 , 3 , 185 .
  • Potdar , M. K. ; Mohile , S. S. ; Salunkhe , M. M. Coumarin syntheses via Pechmann condensation in Lewis acidic chloroaluminate ionic liquid . Tetrahedron Lett. 2001 , 42 , 9285 .
  • Singh , V. ; Kaur , S. ; Sapehiyia , V. ; Singh , J. ; Kad , G. L. Microwave-accelerated preparation of [bmim][HSO4] ionic liquid: An acid catalyst for improved synthesis of coumarins . Catal. Commun. 2005 , 6 , 57 .
  • Hajipour , A. R. ; Kooshki , B. ; Ruoho , A. E. Nitric acid in the presence of supported P2O5 on silica gel: An efficient and novel reagent for oxidation of sulfides to the corresponding sulfoxides . Tetrahedron Lett. 2005 , 46 , 5503 .
  • (a) Hajipour , A. R. ; Arbabian , M. ; Ruoho , A. E. Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions. J. Org. Chem. 2002, 67, 8622; (b) Hajipour , A. R. ; Ruoho , A. E. Iodination of aromatic compounds under mild and solvent-free conditions. Org. Prep. Proced. Int. 2002, 34, 647; (c) Hajipour , A. R. ; Mazloumi , G. An efficient and simple procedure for preparation of esters and anhydrides from acid chlorides in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) under solvent-free conditions. Synth. Commun. 2002, 32, 23; (d) Hajipour , A. R. ; Ruoho , A. E. Oxidation of thiols to the corresponding disulfides with tetramethylammonium chlorochromate under non-aqueous conditions. J. Chem. Res., Synop. , 2002, 547; (e) Hajipour , A. R. ; Adibi , H. ; Ruoho , A. E. Wet silica–supported permanganate for the cleavage of semicarbazones and phenylhydrazones under solvent-free conditions. J. Org. Chem. 2003, 68, 4553; (f) Hajipour , A. R. ; Bagheri , H. ; Ruoho , A. E. Solid-state oxidation of alcohols using 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate. Bull. Korean Chem. Soc. 2004, 25, 1238; (g) Hajipour , A. R. ; Ruoho , A. E. Deprotection of thioacetals by wet alumina–supported Cr(VI) oxide under solvent-free conditions. Sul. Lett. 2002, 25, 151; (h) Hajipour , A. R. ; Mirjalili , B. F. ; Zarei , A. ; Khazdooz , L. ; Ruoho , A. E. A novel method for sulfonation of aromatic rings with silica sulfuric acid. Tetrahedron Lett. 2004, 45, 6607.
  • (a) Hajipour , A. R. ; Mallakpoor , E. ; Imanzadeh , G. A rapid and convenient synthesis of oximes in dry media under microwave irradiation . J. Chem. Res. 1999 , 228; (b) Hajipour , A. R. ; Mallakpoor , E. ; Adibi , H. Benzyltriphenylphosphonium peroxymonosulfate: As a novel and efficient reagent for oxidation of alcohols under solvent-free condition . Chem. Lett. 2000 , 460; (c) Hajipour , A. R. ; Mallakpoor , E. ; Afrousheh , A. A convenient and mild procedure for the synthesis of alkyl p-toluenesulfinates under solvent-free conditions using microwave irradiation . Tetrahedron 1999 , 55 , 2311 ; (d) Hajipour , A. R. ; Islami , F. A convenient and highly diastereoselective synthesis of optically active sulfinate esters from sulfonyl chlorides under solid state conditions . Ind. J. Chem. 1999 , 38B , 461 ; (e) Hajipour , A. R. ; Mallakpoor , E. ; Imanzadeh , G. Oxidation of alcohols to carbonyl compounds under solvent-free conditions using permanganate supported on alumina . Chem. Lett. 1999 , 99; (f) Hajipour , A. R. ; Hantehzadeh , M. Asymmetric reduction of prochiral cyclic imines to alkaloid derivatives by novel asymmetric redusing reagent in THF or under solid-state conditions . J. Org. Chem. 1999 , 64 , 8475 ; (g) Hajipour , A. R. ; Mallakpoor , E. ; Backnejad , H. Benzyltriphenylphosphonium cholorochromate: A mild and novel reagent for oxidation of benzylic and allylic alcohols under non-aqueous and aprotic conditions or microwave conditions . Synth. Commun. 2000 , 30 , 3855 ; (h) Hajipour , A. R. ; Mallakpoor , E. ; Afrousheh , A. One-pot and simple reaction for the synthesis of alkyl p-toluenesulfinate esters under solid-phase conditions . Phosphorus, Sulfur Silicon Relat. Elem. 2000 , 160 , 67 ; (i) Hajipour , A. R. ; Mallakpoor , E. ; Khoee , S. An efficient, fast and selective oxidation of aliphatic and benzylic alcohols to the corresponding carbonyl compounds under microwave irradiation . Synlett 2000 , 740; (j) Hajipour , A. R. ; Baltork , I. M. ; Nikbaghat , K. ; Imanzadeh , Gh. Solid-phase synthesis of oximes . Synth. Commun. 1999 , 29 , 1697 .
  • (a) Hajipour , A. R. ; Mahboubkhah , N. 1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate: A mild and efficient oxidation for the cleavage of oxime double bonds under anhydrous conditions . J. Chem. Res. Synop. 1998 , 122 ; (b) Hajipour , A. R. ; Ruoho , A. E. Solid state deprotection of thioacetals and thioketals using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate and aluminum chloride . Org. Prep. Proced. Int. 2005 , 37 , 298 ; (c) Hajipour , A. R. ; Ruoho , A. E. Methyltriphenylphosphonium peroxydisulfate and iodine as mild reagents for the iodination of activated aromatic compounds . Org. Prep. Proced. Int. 2005 , 37 , 279 .
  • Parvin , T. ; Choudhury , L. H. Silica-supportedp perchloric acid (HClO4-SiO2): A versatile catalyst for tetrahydropyranylation, oxathioacetalization, and thioacetalization . Synthesis , 2006 , 2497 .
  • Kavala , V. ; Samal , A. K. ; Patal , B. K. Water as catalyst and solvent: Tetrahydropyranylation of alcohols in an aqueous medium . Arkivoc , 2005 , 20 .
  • Hajipour , A. R. ; Kargosha , M. ; Ruoho , A. E. Tetrahydropyranylation of alcohols under solvent-free conditions . Synth. Commun. 2009 , 39 , 1084 .

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.