论文信息 - Aluminium Chloride Hexahydrate (AlCl3 · 6H2O): An Efficient, Facile, Mild, And Highly Chemoselective Catalytic Deprotection of Tert-Butyldimethylsilyl (TBS) Ethers

Aluminium Chloride Hexahydrate (AlCl3 · 6H2O): An Efficient, Facile, Mild, And Highly Chemoselective Catalytic Deprotection of Tert-Butyldimethylsilyl (TBS) Ethers

Abstract tert-Butyldimethylsilyl (TBS) phenyl / alkyl ethers were cleaved to the corresponding efficiently parent hydroxyl compounds in good yields using catalytic amounts of AlCl3 · 6H2O by conventional or microwave-assisted heating in methanol or isopropanol solution. Intramolecular and competitive experiments demonstrated the chemoselective deprotection of TBS ethers in the presence of triisopropylsilyl and tert-butyldiphenylsilyl ethers. GRAPHICAL ABSTRACT

[1] Hwan-Jeong Jeong,et al. An efficient and chemoselective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using tailor-made ionic liquid , 2012 .

[2] Bing Wang,et al. LiOAc-catalyzed chemoselective deprotection of aryl silyl ethers under mild conditions. , 2009, The Journal of organic chemistry.

[3] Indresh Kumar,et al. Facile and Highly Selective Deprotection of tert‐Butyldimethyl Silyl Ethers using Sulfated SnO2 as a Solid Catalyst , 2008 .

[4] S. Baskaran,et al. A facile, catalytic, and environmentally benign method for selective deprotection of tert-butyldimethylsilyl ether mediated by phosphomolybdic acid supported on silica gel. , 2005, The Journal of organic chemistry.

[5] R. D. Crouch,et al. Deprotection of silyl ethers using ZnBr2 and H2O in CH2Cl2 , 2002 .

[6] B. Karimi,et al. Aluminum Chloride (Alcl3) Promotes Selective Oxidative Deprotection of Benzylic Trimethylsilyl and Tert- Butyldimethylsilyl Ethers to the Corresponding Carbonyl Compounds with Manganese Dioxide (Mno2) , 1999 .

[7] M. Stieff,et al. Selective Deprotection of Silyl-Protected Phenols Using Solid NaOH and a Phase Transfer Catalyst , 1999 .

[8] Á. Guerrero,et al. Utilization of neutral alumina as a mild reagent for the selective cleavage of primary and secondary silyl ethers , 1994 .