NbCl₅ as an Efficient Catalyst for Chemoselective Synthesis of 1,1-Diacetates Under Solvent-Free Conditions

REFERENCES

• Green , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis; , 3rd ed. ; Wiley : New York , 1999 .
   Google Scholar
• Kochhar , K. S. ; Bal , B. S. ; Deshpande , R. P. ; Rajadhyaksha , S. N. ; Pinnick , H. W. Protecting groups in organic synthesis, part 8: Conversion of aldehydes into geminal diacetates . J. Org. Chem. 1983 , 48 , 1765 – 1767 .
   Web of Science ®Google Scholar
• (a) Sandbery , M. ; Sydnes , L. K. The chemistry of acylals, 3: Cyanohydrin esters from acylals with cyanide reagents . Org. Lett. 2000 , 2 , 687 – 689 ; (b) Sandberg , M. ; Sydnes , L. K. The chemistry of acylals, part II: Formation of nitriles by treatment of acylals with trimethylsilyl azide in the presence of a Lewis acid . Tetrahedron Lett. 1998 , 39 , 6361 – 6364 ; (c) Van Heerden , F. R. ; Huyser , J. J. ; Williams , D. B. G. ; Holzapfer , C. W. Palladium-catalysed substitution reactions of geminal allylic diacetates . Tetrahedron Lett. 1998 , 39 , 5281 – 5284 ; (d) Trost , B. M. ; Lee , C. B. Gem-diacetates as carbonyl surrogates for asymmetric synthesis: Total syntheses of sphingofungins E and F . J. Am. Chem. Soc. 2001 , 123 , 12191 – 12201 ; (e) Trost , B. M. ; Lee , C. B. ; Weiss , J. M. Asymmetric alkylation of allylic gem-dicarboxylates . J. Am. Chem. Soc. 1995 , 117 , 7247 – 7248 .
   PubMed Web of Science ®Google Scholar
• Frick , J. G. ; Harper , R. J. Acetals as crosslinking reagents for cotton . J. Appl. Polym. Sci. 1984 , 29 , 1433 – 1447 .
   Web of Science ®Google Scholar
• (a) Tomita , M. ; Kikuchi , T. ; Bessho , K. ; Hori , T. ; Inubushi , Y. Studies on pilocereine and related compounds III: Synthesis of 2,2′,3-trimethoxy-diphenyl ether-4′,5- and -4′,6-dicarboxaldehyde . Chem. Pharm. Bull. 1963 , 11 , 1484 – 1490 ; (b) Davey , W. ; Gwilt , J. R. Chalcones and related compounds, part I: Preparation of nitro-, amino-, and halogeno-chalcones . J. Chem. Soc. 1957 , 1008 – 1014 ; (c) Freeman , F. ; Karchefski , E. M. Preparation and spectral properties of benzylidene diacetates . J. Chem. Eng. Data 1977 , 22 , 355 – 357 ; (d) Marshall , J. A. ; Wuts , P. G. M. Stereoselective synthesis of racemic occidentalol and related cis-fused hexahydronaphthalenes from m-toluic acid . J. Org. Chem. 1977 , 42 , 1794 – 1798 .
   PubMedGoogle Scholar
• (a) Michie , J. K. ; Miller , J. A. Phosphorus trichloride as catalyst in the preparation of 1,1-diacetates from aldehydes . Synthesis 1981 , 824 ; (b) Yadav , J. S. ; Reddy , B. V. S. ; Srinivas , C. Indium trichloride–catalyzed chemoselective conversion of aldehydes to gem-diacetates . Synth. Commun. 2002 , 32 , 2169 – 2174 ; (c) Smitha , G. ; Reddy , C. S. A facile and efficient ZrCl4-catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage . Tetrahedron 2003 , 59 , 9571 – 9576 : (d) Yadav , J. S. ; Reddy , B. V. S. ; Venugopal , C. ; Ramalingam , T. LiBF4-mediated conversion of aldehydes to gem-diacetates . Synlett 2002 , 604 – 606 ; (e) Chakraborti , A. K. ; Thilagavathi , R. ; Kumar , R. Copper(II) tetrafluoroborate–catalyzed formation of aldehyde-1,1-diacetates . Synthesis 2004 , 831 – 833 ; (f) Roy , S. C. ; Banerjee , B. A mild and efficient method for the chemoselective synthesis of acylals from aldehydes and their deprotections catalysed by ceric ammonium nitrate . Synlett 2002 , 1677 – 1678 ; (g) Karimi , B. ; Ebrahiminan , G. R. ; Seradj , H. Highly efficient and chemoselective conversion of aldehydes to acylals catalyzed with tungsten hexachloride (WCl6) . Synth. Commun. 2002 , 32 , 669 – 673 ; (h) Ranu , B. C. ; Dutta , J. Zinc tetrafluoroborate–catalyzed efficient conversion of aldehydes to geminal diacetates and cyanoacetates . Chem. Lett. 2003 , 32 , 366 – 367 ; (i) Romanelli , G. P. ; Thomas , H. J. ; Baronetti , G. T. ; Autino , J. C. Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells–Dawson acid (H6P2W18O62·24H2O) . Tetrahedron Lett. 2003 , 44 , 1301 – 1303 ; (j) Firouzabadi , H. ; Iranpoor , N. ; Nowrouzi , F. ; Amani , K. Aluminum dodecatungstophosphate (AlPW12O40) as an efficient heterogeneous inorganic catalyst for the chemoselective synthesis of geminal diacetates (acylals) under solvent-free conditions . Tetrahedron Lett. 2003 , 44 , 3951 – 3954 .
   Google Scholar
• (a) Olah , G. A. ; Mehrotra , A. K. Catalysis by solid superacid: Improved nafion-H-catalyzed prepatation of 1,1-diacetates from aldehydes . Synthesis 1982 , 962 – 963 ; (b) Jin , T.-S. ; Du , G.-Y. ; Zhang , Z.-H. ; Li , T.-S. An efficient and convenient procedure for preparation of 1,1-diacetates from aldehydes catalysed by expansive graphite . Synth. Commun. 1997 , 27 , 2261 – 2266 ; (c) Ballini , R. ; Bordoni , M. ; Bosica , G. ; Maggi , R. ; Sartori , G. Solvent-free synthesis and deprotection of 1,1-diacetates over a commercially available zeolite Y as a reusable catalyst . Tetrahedron Lett. 1998 , 39 , 7587 – 7590 ; (d) Pereira , C. ; Gigante , B. ; Marcelo-Curto , M. J. ; Carreyre , H. ; Pérot , G. ; Guisnet , M. Diacetates from aldehyldes in the presence of zeolites . Synthesis 1995 , 1077 – 1078 ; (e) Zhang , Z.-H. ; Li , T.-S. ; Fu , C.-G. Montmorillonite clay catalysis, part 4.11: An efficient and convenient procedure for preparation of 1,1-diacetates from aldehydes . J. Chem. Res., Synop. 1997 , 174 – 175 ; (f) Li , T.-S. ; Zhang , Z.-H. ; Gao , Y.-J. A rapid preparation of acylals of aldehydes catalysed by Fe3+-montmorillonite . Synth. Commun. 1998 , 28 , 4665 – 4671 ; (g) Nagy , N. M. ; Jakab , M. A. ; Konya , J. ; Antus , S. Convenient preparation of 1,1-diacetates from aromatic aldehydes catalysed by zinc-montmorillonite . Appl. Clay Sci. 2002 , 21 , 213 – 216 ; (h) Li , Y.-Q. ; Cheng , L.-H. A rapid and convenient synthesis of acylals from aldehydes and acetic anhydrides catalyzed by SnCl4/SiO2 . Chin. Chem. Lett. 2001 , 12 , 565 – 568 ; (i) Li , Y.-Q . A rapid and convenient synthesis of 1,1-diacetates from aldehydes and acetic anhydride catalyzed by PVC-FeCl3 catalyst . Synth. Commun. 2000 , 30 , 3913 – 3917 ; (j) Raju , S. V. N. Sulfated zirconia: An efficient catalyst for the synthesis of 1,1-diacetates from aldehydes and ketones . J. Chem. Res., Synop. 1996 , 68 ; (k) Jin , T.-S. ; Ma , Y.-R. ; Sun , X. ; Liang , D. ; Li , T.-S. Facile preparation of 1,1-diacetates from aldehydes with acetic anhydride catalysed by TiO2/SO4 2− solid superacid . J. Chem. Res., Synop. 2000 , 96 – 97 ; (l) Jin , T.-S. ; Feng , G.-L. ; Yang , M.-N. ; Li , T.-S. An efficient and practical procedure for synthesis of 1,1-diacetates from aldehydes catalyzed by zirconium sulfate tetrahydrate–silica gel . Synth. Commun. 2004 , 34 , 1645 – 1651 .
   Google Scholar
• Deka , N. ; Kalita , D. J. ; Borah , R. ; Sarma , J. C. Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes. J. Org. Chem. 1997, 62, 1563–1564.
   Web of Science ®Google Scholar
• Karimi , B. ; Seradj , H. ; Ebrahimian , G. R. Mild and efficient conversion of aldehydes to 1,1-diacetates catalyzed with N-bromosuccinimide (NBS) . Synlett 2000 , 623 – 624 .
   Web of Science ®Google Scholar
• Deka , N. ; Borah , R. ; Kalita , D. J. ; Sarma , J. C. Synthesis of 1,1-diacetates from aldehydes using trimethylchlorosilane and sodium iodide as catalyst . J. Chem. Res., Synop. 1998 , 94 – 95 .
   Web of Science ®Google Scholar
• (a) Chandra , K. L. ; Saravanan , P. ; Singh , V. K. An efficient method for diacetylation of aldehydes . Synlett 2000 , 359 – 360 ; (b) Aggarwal , V. K. ; Fonquerna , S. ; Vennall , G. P. Sc(OTf)3, an efficient catalyst for formation and deprotection of geminal diacetates (acylals): Chemoselective protection of aldehydes in presence of ketones . Synlett 1998 , 849 – 850 ; (c) Karimi , B. ; Maleki , J. Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions . J. Org. Chem. 2003 , 68 , 4951 – 4954 .
   Google Scholar
• Wang , R. ; Li , B. G. ; Huang , T.-K. ; Shi , L. ; Lu , X.-X. NbCl5-catalyzed one-pot Mannich-type reaction: Three-component synthesis of β-amino carbonyl compounds . Tetrahedron Lett. 2007 , 48 , 2071 – 2073 .
   Web of Science ®Google Scholar
• Sudo , Y. ; Arai , S. ; Nishida , A. Facile and regioselective dealkylation of alkyl aryl ethers using niobium(V) chloride . Eur. J. Org. Chem. 2006 , 3 , 752 – 758 .
   Web of Science ®Google Scholar
• (a) Andrade , C. K. Z. ; Azevedo , N. R. Niobium(V) chloride–mediated allylation of aldehydes: Scope and stereoselectivity . Tetrahedron Lett. 2001 , 42 , 6473 – 6476 ; (b) Andrade , C. K. Z. ; Azevedo , N. R. ; Oliveira , G. R. NbCl5: A novel Lewis acid in allylation reactions . Synthesis 2002 , 928 – 936 ; (c) Andrade , C. K. Z. ; Oliveira , G. R. Allylation of aldimines promoted by NbCl5 . Tetrahedron Lett. 2002 , 43 , 1935 – 1937 .
   Web of Science ®Google Scholar
• Andrade , C. K. Z. ; Matos , R. A. F. Niobium pentachloride–mediated nucleophilic additions to cyclic N-acyliminium ions . Synlett 2003 , 1189 – 1191 .
   Web of Science ®Google Scholar
• Andrade , C. K. Z. ; Azevedo , N. R. Niobium(V) chloride–mediated allylation of aldehydes: Scope and stereoselectivity . Tetrahedron Lett. 2001 , 42 , 6473 .
   Web of Science ®Google Scholar
• Ma , J. J. ; Zhou , X. ; Zang , X. H. ; Wang , C. ; Wang , Z. ; Li , J. C. ; Li , Q. A green and efficient synthesis of 9-aryl-3,4,5,6,7,9-hexahydroxanthene-1,8-dione using task-specific ionic liquid as dual catalyst and solvent . Aus. J. Chem. 2007 , 60 , 146 – 148 .
   Web of Science ®Google Scholar
• Wang , C. ; Ma , J. J. ; Zhou , X. ; Zang , X. H. ; Wang , Z. ; Gao , Y. J. ; Cui , P. L. 1-n-Butyl-3-methylimmidazolium tetrafluoroborate promoted green synthesis of 5-arylidene barbituric acids and thiobarbituric acids derivatives . Synth. Commun. 2005 , 35 ( 21 ), 2759 – 2764 .
   Web of Science ®Google Scholar
• Ma , J. J. ; Zang , X. H. ; Zhou , X. ; Wang , C. ; Li , J. C. ; Li , Q. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by acidic ionic liquid . Indian J. Chem., Sec. B 2007 , 46 ( 2 ), 2045 – 2048 .
   Google Scholar
• Ma , J. J. ; Gao , S. T. ; Li , Z. ; Tang , R. X. ; Liu , H. Y. ; Wang , C. ; Gao , Y. Synthesis of 5-arylmethylidene-2-thio-4-thiazolidinone derivatives catalyzed by alkaline ionic liquid. Chin. J. Org. Chem. 2008, 28 (2), 339–342.
   Web of Science ®Google Scholar
• Jin , T. S. ; Sun , G. ; Li , Y. W. ; Li , T. S. An efficient and convenient procedure for the preparation of 1,1-diacetates from aldehydes catalyzed by NH2SO3H . Green Chem. 2002 , 4 , 255 – 256 .
   Web of Science ®Google Scholar
• Yin , L. ; Zhang , Z.-H. ; Wang , Y.-M. ; Pang , M.-L. Indium tribromide as a highly efficient and versatile catalyst for chemoselective synthesis of acylals from aldehydes under solvent-free conditions . Synlett 2004 , 1727 – 1730 .
   Web of Science ®Google Scholar
• Hajipour , A. R. ; Zarei , A. ; Khazdooz , L. ; Mirjalili , B. B. F. ; Sheikhan , N. ; Zahmatkesh , S. ; Ruoho , A. E. Silica sulfuric acid as an efficient heterogeneous catalyst for the synthesis of 1,1-diacetates under solvent-free conditions . Synthesis 2005 , 3644 – 3646 .
   Web of Science ®Google Scholar