Green and Efficient Procedure for the Trimethylsilylation of Hydroxy Groups and Their Regeneration Using Sulfamic Acid as Recyclable Catalyst

REFERENCES

• Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis , , 3rd ed. ; John Wiley : New York , 1999 .
   Google Scholar
• Look , G. V. ; Simchen , G. ; Heberle , J. Silylation Agents ; Fluka : Buchs , Switzerland , 1995 .
   Google Scholar
• Dsa , B. A. ; Verkade , J. G. P(MeNCH2CH2)3N: An efficient silylation catalyst . J. Am. Chem. Soc. 1996 , 118 , 12832 – 12833 .
   Google Scholar
• Karimi , B. ; Golshani , B. Mild and highly efficient method for the silylation of alcohols using hexamethyldisilazane catalyzed by iodine under nearly neutral reaction conditions . J. Org. Chem. 2000 , 65 , 7228 – 2144 .
   PubMed Web of Science ®Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Amani , K. ; Nowrouzi , F. Tungstophosphoric acid (H3PW12O40) as a heterogeneous inorganic catalyst: Activation of hexamethyldisilazane (HMDS) by tungstophosphoric acid for efficient and selective solvent-free O-silylation reactions . J. Chem. Soc., Perkin Trans. 1 2002 , 2601 – 2604 .
   Google Scholar
• Akhlaghinia , B. ; Tavakoli , S. An efficient method for the protection of alcohols and phenols by using hexamethyldisilazane in the presence of cupric sulfate pentahydrate under neutral reaction conditions . Synthesis 2005 , 1775 – 1778 .
   Web of Science ®Google Scholar
• Jin , T.-S. ; Lin , R.-F. ; Zhao , Y. ; Li , T.-S. Silica sulfate, an efficient catalyst for the trimethylsilylation of alcohols . Synth. Commun. 2006 , 36 , 1823 – 1828 .
   Web of Science ®Google Scholar
• Shirakawa , E. ; Hironaka , K. ; Otsuka , H. ; Hayashi , T. Palladium-catalyzed silylation of alcohols with hexamethyldisilane . Chem. Commun. 2006 , 3927 – 3929 .
   PubMed Web of Science ®Google Scholar
• Jadhav , V. H. ; Kumar , K. S. A. ; Chaudhari , V. D. ; Dhavale , D. D. Facile method for trimethylsilylation of alcohols using hexamethyldisilazane and ammonium thiocyanate under neutral conditions . Synth. Commun. 2007 , 37 , 1363 – 1370 .
   Web of Science ®Google Scholar
• Shaterian , H. R. ; Shahrekipoor , F. ; Ghashang , M. Silica-supported perchloric acid (HClO4-SiO2): A highly efficient and reusable catalyst for the protection of hydroxyl groups using HMDS under mild and ambient conditions . J. M. Catal. A: Chem. 2007 , 272 , 142 – 151 .
   Web of Science ®Google Scholar
• Moghadam , M. ; Tangestaninejad , S. ; Mirkhani , V. ; Mohammadpoor-Baltork , I. ; Chahardahcheric , S. ; Tavakoli , Z. Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable zirconyl triflate, [ZrO(OTf)2] . J. Organometal. Chem. 2008 , 693 , 2041 – 2046 .
   Web of Science ®Google Scholar
• Shirini , F. ; Zolfigol , M. A. ; Abedini , M. Chemoselective trimethylsilylation of alcohols catalyzed by saccharin sulfonic . Monatsh. Chem. 2009 , 140 , 61 – 64 .
   Web of Science ®Google Scholar
• Yu , Z. ; Vercade , J. G. P(MeNCH2CH2)3N: An efficient catalyst for the desilylation of tert-butyldimethylsilyl ethers . J. Org. Chem. 2000 , 65 , 2065 – 2068 .
   PubMed Web of Science ®Google Scholar
• Wu , Y. J. ; Huang , H. ; Shen , X. ; Hu , Q. ; Tang , C.-J. ; Li , L. Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers. Org. Lett. 2002, 4, 2141–2144.
   PubMedGoogle Scholar
• Lakouraj , M. M. ; Akbari , A. Sulfuric acid supported on silica gel: An efficient catalyst for silylation of hydroxyl groups with HMDS and their convenient deprotection under nonaqueous condition . Ind. J. Chem. Sect. B 2003 , 42 , 1165 – 1167 .
   Google Scholar
• Levin , J. I. ; Du , M. T. ; Park , K. Practical sulfonylation of amines with 4-hydroxybenzenesulfonyl chloride: In situ silylation–desilylation . Synth. Commun. 2004 , 34 , 2773 – 2781 .
   Web of Science ®Google Scholar
• Crouch , R. ; Williams , A. Rapid, acid-mediated deprotection of silyl ethers using microwave heating . Synth. Commun. 2006 , 36 , 959 – 964 .
   Google Scholar
• Clark , J. H. Solid acids for green chemistry . Acc. Chem. Res. 2002 , 35 , 791 – 797 .
   PubMed Web of Science ®Google Scholar
• Wang , B. Sulfamic acid: A very useful catalyst . Synlett 2005 , 1342 – 1343 .
   Web of Science ®Google Scholar
• Wang , B. ; Gu , Y. ; Song , G. ; Yang , T. ; Yang , L. ; Suo , J. An efficient procedure for protection of carbonyls catalyzed by sulfamic acid . J. Mol. Catal. A: Chem. 2005 , 233 , 121 – 126 .
   Google Scholar
• Tao , L. ; Zou , J. ; Zhang , L. L. ; Zhang , Y. Sulfamic acid–catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition . Tetrahedron Lett. 2007 , 48 , 4297 – 4300 .
   Google Scholar
• Kamal , A. ; Rajendra-Prasad , B. ; Malla-Reddy , A. ; Naseer , M. ; Khan , A. Sulfamic acid as an efficient and recyclable catalyst for the ring opening of epoxides with amines and anilines: An easy synthesis of β-amino alcohols under solvent-free conditions . Catal. Commun. 2007 , 8 , 1876 – 1880 .
   Web of Science ®Google Scholar
• Li , Z. ; Sun , Y. ; Ren , X. ; Wei , P. ; Shi , Y. ; Ouyang , P. Sulfamic acid–catalyzed direct condensation of aldehydes, amines, and TMSCN to α-aminonitriles at ambient temperature . Synlett 2007 , 803 – 805 .
   Google Scholar
• Upadhyaya , D. J. ; Barge , A. ; Stefania , R. ; Cravotto , G. Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst . Tetrahedron Lett. 2007 , 48 , 8318 – 8322 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Ranjbar , L. ; Derikvand , F. ; Bamoharram , F. F. Sulfamic acid as a cost-effective catalyst instead of metal-containing acids for the one-pot synthesis of β-acetamido ketones . J. Mol. Catal. A: Chem. 2007 , 276 , 226 – 229 .
   Web of Science ®Google Scholar
• Mitragotri , S. D. ; Pore , D. M. ; Desai , U. V. ; Wadgaonkar , P. P. Sulfamic acid: An efficient and cost-effective solid acid catalyst for the synthesis of α-aminophosphonates at ambient temperature . Catal. Commun. 2008 , 9 , 1822 – 1826 .
   Web of Science ®Google Scholar
• Khazaei , A. ; Rostami , A. ; Raiatzadeh , A. ; Mahboubifar , M. N-Bromosuccinimide (NBS)–selective and effective catalyst for trimethylsilylation of alcohols and phenols using hexamethyldisilazane and their regeneration under mild and neutral reaction conditions . Can. J. Chem. 2007 , 85 , 336 – 340 .
   Web of Science ®Google Scholar
• Khazaei , A. ; Rostami , A. ; Mahboubifar , M. N,N′-Dibromo-N,N′-1,2-ethanediylbis(benzene sulfonamide) as a novel N-bromo reagent catalyzed tetrahydropyranylation/depyranylation of alcohols and phenols under mild conditions . Catal. Commun. 2007 , 8 , 383 – 388 .
   Web of Science ®Google Scholar
• Rostami , A. ; Khazaei , A. ; Mahboubifar , M. ; Rahmati , S. Convenient trimethylsilylation of hydroxy groups with hexamethyldisilazane under solvent-free conditions . Org. Prep. Proc. Inter. 2008 , 40 , 303 – 306 .
   Web of Science ®Google Scholar
• Rostami , A. ; Rahmati , S. ; Khazaei , A. A highly efficient and ecofriendly procedure for tetrahydropyranylation of alcohols and phenols in the presence of in-situ-generated I2 under heterogeneous and neutral conditions . Monatsh. Chem. 2009 , 140 , 663 – 667 .
   Web of Science ®Google Scholar