Pinacol Coupling Reaction of Aromatic Aldehydes Mediated by Aqueous Vanadium(II) Solution Under Ultrasound Irradiation

References

• Robertson , G. M. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B. M. New York : Pergamon .
   Google Scholar
• Rieke , R. D. and Kim , S. H. 1998 . New reagent for reductive coupling of carbonyl and imine compounds: Highly reactive manganese‐mediated pinacol coupling of aryl aldehydes, aryl ketones, and aldimines . J. Org. Chem. , 63 : 5235
   Web of Science ®Google Scholar
• Seyden‐Penne , J. 1995 . Chiral Auxiliaries and Ligands in Asymmetric Synthesis New York : Wiley .
   Google Scholar
• Kammermeier , B. , Beck , G. , Jacobi , D. and Jendralla , H. 1994 . Vanadium(II)‐ and niobium(III)‐induced diastereoselective pinacol coupling of homochiral peptide aldehydes to C2‐symmetic HIV‐protease inhibitors . Angew. Chem., Int. Ed. Engl. , 33 : 685
   Web of Science ®Google Scholar
• Reetz , M. T. and Griebenow , N. 1996 . Synthesis and stereoselective C‒C bond forming reactions of peptide aldehydes . Liebigs Ann. , : 335
   Google Scholar
• Ho , T.‐L. , Henninger , M. and Olah , G. A. 1976 . Reduction of aryl azides to arylamines with vanadium(II) chloride . Synthesis , : 815
   Google Scholar
• Olah , G. A. , Arvanaghi , M. and Prakash , G. K. S. 1980 . Reductive cleavage of oximes with vanadium(II) chloride . Synthesis , : 220
   Google Scholar
• Inokuchi , T. , Kawafuchi , H. and Torii , S. 1991 . Vanadium(II)‐promoted cyclization of 5,6‐enals or 5,6‐ynals. A stereoselective approach to trans‐2‐alkyl or trans‐2‐alkylidenecyclopentanols . J. Org. Chem. , 56 : 4983
   Web of Science ®Google Scholar
• Hirao , T. , Hirano , K. , Hasegawa , T. , Ohshiro , Y. and Ikeda , I. 1993 . A novel system consisting of low‐valent vanadium and diethyl phosphonate or triethyl phosphite for the highly stereoselective reduction of gem‐dibromocyclopropanes . J. Org. Chem. , 58 : 6529
   Web of Science ®Google Scholar
• Takahara , P. M. , Freudenberger , J. H. , Konradi , A. W. and Pedersen , S. F. 1989 . Intermolecular pinacol cross coupling of aryl aldehydes or their dimethyl acetals with non‐aryl aldehydes . Tetrahedron Lett. , 30 : 7177
   Web of Science ®Google Scholar
• Konradi , A. W. and Pedersen , S. F. 1990 . Stereoselective synthesis of 3‐amino 1,2‐diols via intermolecular pinacol cross‐coupling of α‐[(alkoxycarbonyl) amino] aldehydes with aliphatic aldehydes. Short asymmetric syntheses of two 2,3,6‐trideoxy‐3‐amino sugars . J. Org. Chem. , 55 : 4506
   Web of Science ®Google Scholar
• Park , J. and Pedersen , S. F. 1990 . A stereospecific synthesis of 3,3‐disubstituted allylic alcohols. The intermolecular pinacol cross‐coupling reaction between α,α‐disubstituted α‐(diphenylphosphinoyl) acetaldehydes (Ph2P(O)CR1R2CHO) and saturated aldehydes . J. Org. Chem. , 55 : 5924
   Web of Science ®Google Scholar
• Annunziata , R. , Cinquini , M. , Cozzi , F. , Giaroni , P. and Benaglia , M. 1991 . Diastereo‐ and enantioselective synthesis of 1,2‐diols by vanadium(II) promoted pinacol cross coupling . Tetrahedron , 47 : 5737
   Web of Science ®Google Scholar
• Raw , A. S. and Pedersen , S. F. 1991 . Synthesis of cis‐1,2‐cyclobutanediols via intramolecular pinacol coupling of 4‐oxo aldehydes . J. Org. Chem. , 56 : 830
   Web of Science ®Google Scholar
• Kempf , D. J. , Sowin , T. J. , Doherty , E. M. , Hannick , S. M. , Codavoci , L. , Henry , R. F. , Green , B. E. , Spanton , S. G. and Norbeck , D. W. 1992 . Stereocontrolled synthesis of C2‐symmetric and pseudo‐C2‐symmetric diamino alcohols and diols for use in HIV protease inhibitors . J. Org Chem. , 57 : 5692
   Web of Science ®Google Scholar
• Konradi , A. W. and Pedersen , S. F. 1992 . Pinacol homocoupling of (s)‐2‐[n‐(benzyloxycarbonyl) amino] aldehydes by [V2Cl3(THF)6]2[Zn2Cl6] synthesis of C2‐symmetric (1S, 2R, 3R, 4S)‐1,4‐diamino 2,3‐diols . J. Org. Chem. , 57 : 28
   Web of Science ®Google Scholar
• Kraynack , E. A. and Pedersen , S. F. 1993 . Intermolecular pinacol coupling of sulfur‐substituted aldehydes by [V2Cl3(THF)6]2(Zn2Cl6). The effect of the substitution at sulfur on the stereochemical outcome of the pinacol reaction . J. Org. Chem. , 58 : 6114
   Web of Science ®Google Scholar
• Conant , J. B. and Cutter , H. B. 1926 . The irreversible reduction of organic compounds II. The dimolecular reduction of carbonyl compounds by vanadous and chromous salts . J. Am. Chem. Soc. , 48 : 1016
   Google Scholar
• Freudenberger , J. H. , Konradi , A. W. and Pedersen , S. F. 1989 . Intermolecular pinacol cross coupling of electronically similar aldehydes. An efficient and stereoselective synthesis of 1,2‐diols employing a practical vanadium(II) reagent . J. Am. Chem. Soc. , 111 : 8014
   Web of Science ®Google Scholar
• Hirao , T. , Asahara , M. , Muguruma , Y. and Ogawa , A. 1998 . Highly diastereoselective pinacol coupling reaction of secondary aliphatic aldehydes induced by a catalytic system consisting of vanadium complex, chlorosilane, and zinc metal . J. Org. Chem. , 63 : 2812
   Web of Science ®Google Scholar
• Hirao , T. , Hatano , B. , Imamoto , Y. and Ogawa , A. 1999 . A catalytic system consisting of vanadium, chlorosilane, and aluminum metal in the stereoselective pinacol coupling reaction of benzaldehyde derivatives . J. Org. Chem. , 64 : 7665
   Web of Science ®Google Scholar
• Mason , T. J. 1991 . Practical Sonochemistry New York : Ellis Horwood Limited .
   Google Scholar
• Mečarová , M. , Toma , Ś. and Babiak , P. 2001 . Pinacol synthesis in aqueous media . Chem. Paper. , 55 : 302
   Web of Science ®Google Scholar
• Lim , H. J. , Keum , G. , Kang , S. B. , Chung , B. Y. and Kim , Y. 1998 . Indium mediated pinacol coupling reaction of aromatic aldehydes in aqueous media . Tetrahedron Lett. , 39 : 4367
   Web of Science ®Google Scholar
• Basu , M. K. , Becker , F. F. and Banik , B. K. 2000 . Ultrasound‐promoted samarium/ammonium chloride mediated reductive coupling of aromatic ketones . J. Chem. Research, Synop. , : 406
   Google Scholar
• Mečarová , M. and Toma , Ś. 1999 . Optimization of pinacol coupling in aqueous media . Green Chem. , : 257
   Web of Science ®Google Scholar
• Li , J. T. , Bian , Y. J. , Zang , H. J. and Li , T. S. 2002 . Pinacol coupling of aromatic aldehydes and ketones using magnesium in aqueous ammonium chloride under ultrasound . Synth. Commun. , 32 : 547
   Web of Science ®Google Scholar
• Bian , Y. J. , Li , J. T. , Zang , H. J. and Li , T. S. 2002 . Pinacol coupling of aromatic aldehydes and ketones using aluminum under ultrasound . Synth. Commun. , 32 : 1169
   Web of Science ®Google Scholar
• Li , J. T. , Bian , Y. J. , Liu , S. M. and Li , T. S. 2003 . Reductive coupling of aromatic aldehydes using manganese under ultrasound irradiation . Chin. J. Org. Chem. , 23 : 479
   Google Scholar
• Sprich , J. D. and Lewandos , G. S. 1983 . Sonochemical removal of absorbed water and alcohol from magnesium surfaces . Inorg. Chim. Acta. , 76 ( 4 ) : 241
   Web of Science ®Google Scholar
• Mukaiyama , T. , Yoshimura , T. , Igarashi , K. and Kagayama , A. 2001 . Efficient diastereoselective pinacol coupling reaction of aliphatic and aromatic aldehydes by using newly utilized low valent titanium bromide and iodide species . Tetrahedron. , 57 : 2499
   Web of Science ®Google Scholar
• Li , T. Y. , Cui , W. , Liu , J. G. , Zhao , J. Z. and Wang , Z. M. 2000 . A highly dl‐stereoselective pinacolization of aromatic aldehydes mediated by TiCl4‐Zn . J. Chem. Soc., Chem. Commun. , : 139
   Google Scholar