Silica‐Gel‐Supported Aluminium Chloride: A Stable, Efficient, Selective, and Reusable Catalyst for Tetrahydropyranylation of Alcohols and Phenols

References

• Greene , T. W. and Wuts , P. G. M. 2000 . Protective Groups in Organic Synthesis 17 – 292 . New York : John Wiley and Sons .
   Google Scholar
• Miyashita , M. , Yoshikoshi , A. and Grieco , P. A. 1977 . Pyridinium p‐toluenesulfonate: A mild and efficient catalyst for the tetrahydropyranylation of alcohols . J. Org. Chem. , 42 : 3772 – 3774 .
   Web of Science ®Google Scholar
• Bongini , A. , Cardillo , G. , Orena , M. and Sandri , S. 1979 . A simple and practical method for tetrahydropyranylation of alcohols and phenols . Synthesis , : 618 – 620 .
   Web of Science ®Google Scholar
• Molnar , A. and Beregszaszi , T. 1996 . Mild and efficient tetrahydropyranylation and deprotection of alcohols catalyzed by heteropoly acids . Tetrahedron Lett. , 37 : 8597 – 8600 .
   Web of Science ®Google Scholar
• Ravindranath , N. , Ramesh , C. and Biswanath , D. 2001 . Simple, facile and highly selective tetrahydropyranylation of alcohols using silica chloride . Synlett , 11 : 1777 – 1778 .
   Google Scholar
• Namboodriri , V. V. and Varma , R. S. 2002 . Microwave‐assisted preparation of dialkylimidazolium tetrachloroaluminates and their use as catalysts in the solvent‐free tetrahydropyranylation of alcohols and phenols . Chem. Commun. , : 342 – 343 .
   PubMed Web of Science ®Google Scholar
• Karimi , B. and Maleki , J. 2002 . Lithium triflate (LiOTf) catalyzed efficient and chemoselective tetrahydropyranylation of alcohols and phenols under mild and neutral reaction conditions . Tetrahedron Lett. , 43 : 5353 – 5355 .
   Web of Science ®Google Scholar
• Watahiki , T. , Kikumoto , H. , Matsuzaki , M. , Suzuki , T. and Oriyama , T. 2002 . A novel and efficient method for the synthesis of tetrahydropyranyl ethers catalyzed by Sc(OTf)3 . Bull. Chem. Soc. Jpn. , 75 : 367 – 368 .
   Web of Science ®Google Scholar
• Namboodiri , V. V. and Varma , R. S. 2002 . Solvent‐free tetrahydropyranylation (THP) of alcohols and phenols and their regeneration by catalytic aluminium chloride hexahydrate . Tetrahedron Lett. , 43 : 1143 – 1146 .
   Web of Science ®Google Scholar
• Tamami , B. and Parvanak Borujeny , K. 2004 . Chemoselective tetrahydropyranylation of alcohols and phenols using polystyrene supported aluminium chloride as a catalyst . Tetrahedron Lett. , 45 : 715 – 718 .
   Web of Science ®Google Scholar
• Ledneczki , I. , Daranyi , M. , Fulop , F. and Molnar , A. 2005 . SAC‐13 silica nanocomposite solid acid catalyst in organic synthesis . Catal. Today , 100 : 437 – 440 .
   Web of Science ®Google Scholar
• Kim , Y. J. and Varma , R. S. 2005 . Microwave‐assisted preparation of imidazolium‐based tetrachloroindate(III) and their application in the tetrahydropyranylation of alcohols . Tetrahedron Lett. , 46 : 1467 – 1469 .
   Web of Science ®Google Scholar
• Karimi , B. and Khalkhali , M. 2005 . Solid silica‐based sulfonic acid as an efficient and recoverable interphase catalyst for selective tetrahydropyranylation of alcohols and phenols . J. Mol. Catal. A , 232 : 113 – 117 .
   Web of Science ®Google Scholar
• Nishiguchi , T. , Kawamine , K. and Ohtsuka , T. 1992 . Highly selective monoetherification of symmetrical diols catalysed by metallic sulfate supported on silica gel . Chem. Soc., Perkin Trans. 1 , : 153 – 156 .
   Google Scholar
• Nishiguchi , T. , Fujisaki , S. , Kuroda , M. , Kajisaki , K. and Saitoh , M. 1998 . Selective monotetrahydropyranylation of symmetrical diols catalyzed by ion‐exchange resins . J. Org. Chem. , 63 : 8183 – 8187 .
   Web of Science ®Google Scholar
• Deka , N. and Sarma , J. C. 2001 . Microwave‐mediated selective monotetrahydropyranylation of symmetrical diols catalyzed by iodine . J. Org. Chem. , 66 : 1947 – 1948 .
   PubMed Web of Science ®Google Scholar
• Smith , K. 1992 . Solid Supports and Catalysts in Organic Synthesis Chichester, , U.K. : Ellis Horwood .
   Google Scholar
• Ley , S. V. , Baxendale , I. R. , Bream , R. N. , Jackson , P. S. , Leach , A. G. , Longbottom , D. A. , Nesi , M. , Scott , J. S. , Storer , R. I. and Taylor , S. J. 2000 . Multi‐step organic synthesis using solid‐supported reagents and scavengers: A new paradigm in chemical library generation . J. Chem. Soc., Perkin Trans 1 , : 3815 – 4195 .
   Google Scholar
• Tamami , B. and Parvanak Borujeny , K. 2003 . Chemoselective protection of carbonyl compounds as dithioacetals using silica gel supported aluminium chloride . Synth. Commun. , 33 : 4253 – 4258 .
   Web of Science ®Google Scholar
• Parvanak Borujeny , K. 2005 . Conversion of oxiranes to thiiranes catalyzed with silica gel–supported aluminium chloride . Synth. Commun. , 35 : 2575 – 2579 .
   Google Scholar
• Getty , E. E. and Drago , R. S. 1990 . Preparation, characterization, and catalytic activity of a new solid acid catalyst system . Inorg. Chem. , 29 : 1186 – 1192 .
   Web of Science ®Google Scholar