A SIMPLE METHOD FOR MILD OXIDATION OF α-HYDROXYSILANES TO PROVIDE AROYLSILANES

REFERENCES

• Saleur , D. , Bouillon , J.-P. and Portella , C. 1999 . Tetrahedron Lett. , 40 : 321
   Google Scholar
• Saleur , D. , Bouillon , J.-P. and Portella , C. 2000 . Tetrahedron Lett. , 41 : 1885
   Google Scholar
• Tsai , Y. M. , Cherng , C. D. , Nieh , H. C. and Sieh , J. A. 1999 . Tetrahedron , 55 : 14587
   Web of Science ®Google Scholar
• Takeda , K. and Ohtani , Y. 1999 . Org. Lett. , 1 : 677
   Web of Science ®Google Scholar
• Chuang , T.-H. , Fang , J.-M. , Jiaang , W.-T. and Tsai , Y.-M. 1996 . J. Org. Chem. , 61 : 1794
   PubMed Web of Science ®Google Scholar
• Chang , S. Y. , Jiaang , W. T. , Cherng , C. D. , Tang , K. H. , Huang , C. H. and Tsai , Y. M. 1997 . J. Org. Chem. , 62 : 9089
   Web of Science ®Google Scholar
• Tsai , Y. M. , Tang , K. H. and Jiaang , W. T. 1996 . Tetrahedron Lett. , 37 : 7767
   Web of Science ®Google Scholar
• Nakada , M. , Urano , Y. , Kobayashi , S. and Ohno , M. 1994 . Tetrahedron Lett. , 35 : 741
   Web of Science ®Google Scholar
• Fleming , I. , Barbero , A. and Walter , D. 1997 . Chem. Rev. , 97 : 995
   Google Scholar
• Bonini , B. F. , Comes-Franchini , M. , Laboroi , F. , Mazzanti , G. , Ricci , A. and Varchi , G. 1999 . J. Org. Chem. , 64 : 8008
   Web of Science ®Google Scholar
• Huang , A. X. , Xiong , Z. and Corey , E. J. 1999 . J. Am. Chem. Soc. , 121 : 9999
   Web of Science ®Google Scholar
• Patrocínio , A. F. , Corrêa , I. R. Jr. and Moran , P. J.S. 1999 . J. Chem. Soc. Perkin Trans. 1 , : 3133
   Google Scholar
• Tacke , R. and Linoh , H. 1989 . “ Chap. 18 ” . In The Chemistry of Organic Silicon Compounds Edited by: Patai , S. and Rappoport , Z. John Wiley & Sons Ltd. .
   Google Scholar
• Syldatk , C. , Stoffregen , A. , Wuttke , F. and Tacke , R. 1988 . Biotech. Letters , 10 : 731
   Web of Science ®Google Scholar
• Fischer , L. , Wagner , S. A. and Tacke , R. 1995 . Appl. Microbiol. Biotechnol. , 42 : 671
   PubMed Web of Science ®Google Scholar
• Tacke , R. , Wagner , S. A. , Brakmann , S. and Wuttke , F. 1993 . J. Organomet. Chem. , 458 : 13
   Web of Science ®Google Scholar
• Brook , A. G. 1968 . Advance Organometallic Chemistry Edited by: Stone , F. G.A. and West , R. Vol. 7 , 95 N.Y. : Ac. Press .
   Google Scholar
• Page , P. C.B. , Klair , S. S. and Rosenthal , S. 1990 . Chem. Soc. Rev. , 19 : 147
   Web of Science ®Google Scholar
• Ricci , A. and Degl'Innocenti , A. 1989 . Synthesis , : 647
   Google Scholar
• Ricci , A. J. 1998 . Organomet. Chem. , 567 : 181
   Web of Science ®Google Scholar
• Patrocinio , A. F. and Moran , P. J.S. 2001 . J. Braz. Chem. Soc. , 12 : 7
   Web of Science ®Google Scholar
• Patrocínío , A. F. and Moran , P. J.S. 2000 . J. Organomet. Chem. , 603 : 220 For some examples of acylsilanes synthesis methodologies see Ref. [5a], [5b], [5c], [5d], [5e] and for other more recents see
   Web of Science ®Google Scholar
• Tius , M. A. and Hu , H. 1998 . Tetrahedron Lett. , 39 : 5937
   Web of Science ®Google Scholar
• Stergiades , I. A. and Tius , M. A. 1999 . J. Org. Chem. , 64 : 7547
   Web of Science ®Google Scholar
• Geng , F. and Maleczka , R. E. Jr. 1999 . Tetrahedron Lett. , 40 : 3113
   Web of Science ®Google Scholar
• Fleming , I. and Ghosh , U. 1994 . J. Chem. Soc. Perkin Trans. 1 , : 257
   Google Scholar
• Paredes , M. D. and Alonso , R. 1999 . Tetrahedron Lett. , 40 : 3973
   Web of Science ®Google Scholar
• Bonini , B. F. , Franchini , M. C. , Mazzanti , G. , Passamonti , U. , Ricci , A. and Zani , P. 1995 . Synthesis , : 92
   Web of Science ®Google Scholar
• Sakaguchi , K. , Mano , H. and Ohfune , Y. 1998 . Tetrahedron Lett. , 39 : 4311
   Web of Science ®Google Scholar
• Sommer , L. H. , Bailey , D. L. , Golberg , G. M. , Buck , C. E. , Bye , T. S. , Evans , F. J. and Whitmore , F. C. 1954 . J. Am. Chem. Soc. , 76 : 1613
   Web of Science ®Google Scholar
• Ireland , R. E. and Norbeck , D. W. 1985 . J. Org. Chem. , 50 : 2198
   Web of Science ®Google Scholar
• Linderman , R. J. and Suhr , Y. 1998 . J. Org. Chem. , 53 : 31569
   Google Scholar
• Danheiser , R. L. , Fink , D. M. , Okano , K. , Tsai , Y.-M. and Szczepanski , S. W. 1985 . J. Org. Chem. , 50 : 5393
   Web of Science ®Google Scholar
• Huber , P. , Bratovanov , S. , Bienz , S. , Syldatk , C. and Pietzsch , M. 1996 . Tetrahedron: Asymmetry , 7 : 69
   Google Scholar
• Mori , A. , Fujita , A. , Ikegashira , K. , Nishihara , Y. and Hiyama , T. 1997 . Synlett , : 693 The α-silyl alcohols where prepared by addition of trimethyl- or dimethylphenylsilyl lithium to aldehydes. For preparation details and other methods see
   Web of Science ®Google Scholar
• Wilson , S. R. , Hague , M. S. and Misra , R. N. 1982 . J. Org. Chem. , 47 : 747
   Web of Science ®Google Scholar
• Barretm , A. G.M. , Hill , J. M. , Wallace , E. M. and Flygare , J. A. 1991 . Synlett , : 764
   Web of Science ®Google Scholar
• Hudrlik , P. F. , Abdallah , Y. M. , Kulkarni , A. K. and Hudrlik , A. M. 1992 . J. Org. Chem. , 57 : 6552
   Web of Science ®Google Scholar
• Hiyama , T. and Obayashi , M. 1983 . J. Org. Chem. , 48 : 912
   Web of Science ®Google Scholar
• Linderman , R. J. and Ghannam , A. 1990 . J. Am. Chem. Soc. , 112 : 2392
   Web of Science ®Google Scholar
• Linderman , R. J. and Chen , K. 1992 . Tetrahedron Lett. , 33 : 6767
   Web of Science ®Google Scholar
• Regen , S. L. and Koteel , C. 1977 . J. Am. Chem. Soc. , 99 : 3837 The efficiency of supported reagents for better performance in oxidations is known. Examples are: molecular sieves-permanganate
   Web of Science ®Google Scholar
• Menger , F. M. and Lee , C. 1979 . J. Org. Chem. , 44 : 3446 copper sulfatepermanganate
   Web of Science ®Google Scholar
• Oliveira Filho , A. P. , Moreira , B. G. , Moran , P. J.S. and Rodrigues , J. A.R. 1996 . Tetrahedron Lett. , 37 : 5029 montmorillonite-acylnitrates
   Web of Science ®Google Scholar
• Lee , D. G. , Chen Tao and Zhao Wang . 1993 . J. Org. Chem. , 58 : 2918 Also, it is known that potassium permanganate supported onto acidic alumina is a good procedure to obtain aldehydes from olefins cleavage
   Web of Science ®Google Scholar
• Patrocínio , A. F. and Moran , P. J. S. 2000 . Synth. Commun. , 30 : 1419
   Web of Science ®Google Scholar
• General procedure for supported two-phase oxidation. A powdered KMnO4 (0.35 g) and neutral Alumina (0.45 g) were added to water (3.0 mL) and this mixture was stirred by 3 min. followed by addition of hexane (7.0 mL). Thus, the α-silyl alcohol (0.58 mmol) dissolved in 1.0 mL of hexane was added, at room temperature. The mixture was stirred for more 1–5 hours and then filtered under reduced pressure. The organic phase was isolated and the desired product purified by filtration in a short chromatograph column, using hexane-ethyl acetate (9:1)
   Google Scholar
• Physical data of the aroylsilane 4-methoxybenzoyldimethylphenylsilane 2b (R′ = Ph), yellow oil, νmax(KBr)/cm−1 1588 (C = O), 1423, 1511, 1253, 836. NMR 1H (300MHz, CDCl3): 0.61 (s, 6H, SiMe2); 3.82 (s, 3H, OMe); 6.86 (d, J = 9.4 Hz, 1Hmeta); 7.30 − 7.61(m, 5H, SiPh); 7.75 (d, J = 9.4Hz, 1Hortho). m/z: 270 (M• +, 10 %); 269(31); 255(5); 239(16); 135(100). HRMS found m/z 269.09961; calcd. for C16H17O2Si[M-H]+: 269.09978. Physical data of the aroylsilane 3,4-dimethoxybenzoyldimethylphenylsilane 2c (R′ = Ph), yellow oil, νmax(KBr)/cm−1 1573(C = O), 1506, 1413, 1259, 826. NMR 1H (300 MHz, CDCl3): 0.61(s, 6H, SiMe2); 3.78 (s, 3H, OMe); 3.88 (s, 3H, OMe); 6.80 (dd, J = 14.5 and 1.9, lHmeta); 7.30 − 7.41 (m, 5H, SiPh); 7.57 − 7.63(m, 2Hortho). m/z: 300 (M• +, 10 %); 299(22); 285(5); 269(41); 135(100). HRMS found m/z 300.11814; calcd. for C17H20O3Si[M]+: 300.11817. The other acylsilanes 2 were analyzed by GC/MScompar ing the retention time and MSspectra with genuine samples. The physical data of these acylsilanes are found in Ref. [4a], 4e-5a and references cited therein
   Google Scholar