메뉴 건너뛰기




Volumn 35, Issue 18, 2005, Pages 2387-2394

Pinacol coupling reaction of aromatic aldehydes mediated by aqueous vanadium(II) solution under ultrasound irradiation

Author keywords

Aqueous vanadium(II) solution; Pinacol coupling; Ultrasound irradiation

Indexed keywords

ALDEHYDE; VANADIUM;

EID: 25144470554     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910500187787     Document Type: Article
Times cited : (9)

References (32)
  • 2
    • 0001339077 scopus 로고    scopus 로고
    • New reagent for reductive coupling of carbonyl and imine compounds: Highly reactive manganese-mediated pinacol coupling of aryl aldehydes, aryl ketones, and aldimines
    • (b) Rieke, R. D.; Kim, S. H. 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. 1998, 63, 5235.
    • (1998) J. Org. Chem. , vol.63 , pp. 5235
    • Rieke, R.D.1    Kim, S.H.2
  • 5
    • 33748900027 scopus 로고    scopus 로고
    • Synthesis and stereoselective C-C bond forming reactions of peptide aldehydes
    • (b) Reetz, M. T.; Griebenow, N. Synthesis and stereoselective C-C bond forming reactions of peptide aldehydes. Liebigs Ann. 1996 (3), 335.
    • (1996) Liebigs Ann. , Issue.3 , pp. 335
    • Reetz, M.T.1    Griebenow, N.2
  • 6
    • 0008813468 scopus 로고
    • Reduction of aryl azides to arylamines with vanadium(II) chloride
    • (a) Ho, T.-L.; Henninger, M.; Olah, G. A. Reduction of aryl azides to arylamines with vanadium(II) chloride. Synthesis 1976, 815;
    • (1976) Synthesis , pp. 815
    • Ho, T.-L.1    Henninger, M.2    Olah, G.A.3
  • 7
    • 0002417456 scopus 로고
    • Reductive cleavage of oximes with vanadium(II) chloride
    • (b) Olah, G. A.; Arvanaghi, M.; Prakash, G. K. S. Reductive cleavage of oximes with vanadium(II) chloride. Synthesis 1980, 220;
    • (1980) Synthesis , pp. 220
    • Olah, G.A.1    Arvanaghi, M.2    Prakash, G.K.S.3
  • 8
    • 0001028387 scopus 로고
    • Vanadium(II)-promoted cyclization of 5,6-enals or 5,6-ynals. A stereoselective approach to irani-2-alkyl or trans-2-alkylidenecyclopentanols
    • (c) Inokuchi, T.; Kawafuchi, H.; Torii, S. Vanadium(II)-promoted cyclization of 5,6-enals or 5,6-ynals. A stereoselective approach to irani-2-alkyl or trans-2-alkylidenecyclopentanols. J. Org. Chem. 1991, 56, 4983;
    • (1991) J. Org. Chem. , vol.56 , pp. 4983
    • Inokuchi, T.1    Kawafuchi, H.2    Torii, S.3
  • 9
    • 0010918143 scopus 로고
    • A novel system consisting of low-valent vanadium and diethyl phosphonate or triethyl phosphite for the highly stereoselective reduction of gem-dibromocyclopropanes
    • (d) Hirao, T.; Hirano, K.; Hasegawa, T.; Ohshiro, Y.; Ikeda, I. 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. 1993, 58, 6529.
    • (1993) J. Org. Chem. , vol.58 , pp. 6529
    • Hirao, T.1    Hirano, K.2    Hasegawa, T.3    Ohshiro, Y.4    Ikeda, I.5
  • 10
    • 0024820540 scopus 로고
    • Intermolecular pinacol cross coupling of aryl aldehydes or their dimethyl acetals with non-aryl aldehydes
    • (a) Takahara, P. M.; Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. Intermolecular pinacol cross coupling of aryl aldehydes or their dimethyl acetals with non-aryl aldehydes. Tetrahedron Lett. 1989, 30, 7177;
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7177
    • Takahara, P.M.1    Freudenberger, J.H.2    Konradi, A.W.3    Pedersen, S.F.4
  • 11
    • 0001165485 scopus 로고
    • 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
    • (b) Konradi, A. W.; Pedersen, S. F. 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. 1990, 55, 4506;
    • (1990) J. Org. Chem. , vol.55 , pp. 4506
    • Konradi, A.W.1    Pedersen, S.F.2
  • 13
    • 0025787055 scopus 로고
    • Diastereo- and enantioselective synthesis of 1,2-diols by vanadium(II) promoted pinacol cross coupling
    • (d) Annunziata, R.; Cinquini, M.; Cozzi, F.; Giaroni, P.; Benaglia, M. Diastereo- and enantioselective synthesis of 1,2-diols by vanadium(II) promoted pinacol cross coupling. Tetrahedron 1991, 47, 5737;
    • (1991) Tetrahedron , vol.47 , pp. 5737
    • Annunziata, R.1    Cinquini, M.2    Cozzi, F.3    Giaroni, P.4    Benaglia, M.5
  • 14
    • 0001095989 scopus 로고
    • Synthesis of cis-1,2-cyclobutanediols via intramolecular pinacol coupling of 4-oxo aldehydes
    • (e) Raw, A. S.; Pedersen, S. F. Synthesis of cis-1,2-cyclobutanediols via intramolecular pinacol coupling of 4-oxo aldehydes. J. Org. Chem. 1991, 56, 830;
    • (1991) J. Org. Chem. , vol.56 , pp. 830
    • Raw, A.S.1    Pedersen, S.F.2
  • 16
    • 0001965855 scopus 로고
    • 2-symmetric (1S, 2R, 3R, 4S)-1,4-diamino 2,3-diols
    • 2-symmetric (1S, 2R, 3R, 4S)-1,4-diamino 2,3-diols. J. Org. Chem. 1992, 57, 28;
    • (1992) J. Org. Chem. , vol.57 , pp. 28
    • Konradi, A.W.1    Pedersen, S.F.2
  • 17
    • 0005604531 scopus 로고
    • 6). The effect of the substitution at sulfur on the stereochemical outcome of the pinacol reaction
    • 6). The effect of the substitution at sulfur on the stereochemical outcome of the pinacol reaction. J. Org. Chem. 1993, 58, 6114.
    • (1993) J. Org. Chem. , vol.58 , pp. 6114
    • Kraynack, E.A.1    Pedersen, S.F.2
  • 18
    • 0001567274 scopus 로고
    • The irreversible reduction of organic compounds II. The dimolecular reduction of carbonyl compounds by vanadous and chromous salts
    • Conant, J. B.; Cutter, H. B. The irreversible reduction of organic compounds II. The dimolecular reduction of carbonyl compounds by vanadous and chromous salts. J. Am. Chem. Soc. 1926, 48, 1016.
    • (1926) J. Am. Chem. Soc. , vol.48 , pp. 1016
    • Conant, J.B.1    Cutter, H.B.2
  • 19
    • 0000550365 scopus 로고
    • Intermolecular pinacol cross coupling of electronically similar aldehydes. An efficient and stereoselective synthesis of 1,2-diols employing a practical vanadium(II) reagent
    • Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. 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. 1989, 111, 8014.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8014
    • Freudenberger, J.H.1    Konradi, A.W.2    Pedersen, S.F.3
  • 20
    • 2442536248 scopus 로고    scopus 로고
    • Highly diastereoselective pinacol coupling reaction of secondary aliphatic aldehydes induced by a catalytic system consisting of vanadium complex, chlorosilane, and zinc metal
    • Hirao, T.; Asahara, M.; Muguruma, Y.; Ogawa, A. 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. 1998, 63, 2812.
    • (1998) J. Org. Chem. , vol.63 , pp. 2812
    • Hirao, T.1    Asahara, M.2    Muguruma, Y.3    Ogawa, A.4
  • 21
    • 0033214637 scopus 로고    scopus 로고
    • A catalytic system consisting of vanadium, chlorosilane, and aluminum metal in the stereoselective pinacol coupling reaction of benzaldehyde derivatives
    • Hirao, T.; Hatano, B.; Imamoto, Y.; Ogawa, A. A catalytic system consisting of vanadium, chlorosilane, and aluminum metal in the stereoselective pinacol coupling reaction of benzaldehyde derivatives. J. Org. Chem. 1999, 64, 7665.
    • (1999) J. Org. Chem. , vol.64 , pp. 7665
    • Hirao, T.1    Hatano, B.2    Imamoto, Y.3    Ogawa, A.4
  • 24
    • 0032507940 scopus 로고    scopus 로고
    • Indium mediated pinacol coupling reaction of aromatic aldehydes in aqueous media
    • Lim, H. J.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Indium mediated pinacol coupling reaction of aromatic aldehydes in aqueous media. Tetrahedron Lett. 1998, 39, 4367.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4367
    • Lim, H.J.1    Keum, G.2    Kang, S.B.3    Chung, B.Y.4    Kim, Y.5
  • 25
    • 0033770860 scopus 로고    scopus 로고
    • Ultrasound-promoted samarium/ammonium chloride mediated reductive coupling of aromatic ketones
    • Basu, M. K.; Becker, F. F.; Banik, B. K. Ultrasound-promoted samarium/ammonium chloride mediated reductive coupling of aromatic ketones. J. Chem. Research, Synop. 2000, 406.
    • (2000) J. Chem. Research, Synop. , pp. 406
    • Basu, M.K.1    Becker, F.F.2    Banik, B.K.3
  • 26
    • 0040626374 scopus 로고    scopus 로고
    • Optimization of pinacol coupling in aqueous media
    • Mečarová, M.; Toma, Ś. Optimization of pinacol coupling in aqueous media. Green Chem. 1999, 257.
    • (1999) Green Chem. , pp. 257
    • Mečarová, M.1    Toma, Ś.2
  • 27
    • 0036186327 scopus 로고    scopus 로고
    • Pinacol coupling of aromatic aldehydes and ketones using magnesium in aqueous ammonium chloride under ultrasound
    • (a) Li, J. T.; Bian, Y. J.; Zang, H. J.; Li, T. S. Pinacol coupling of aromatic aldehydes and ketones using magnesium in aqueous ammonium chloride under ultrasound. Synth. Commun. 2002, 32, 547;
    • (2002) Synth. Commun. , vol.32 , pp. 547
    • Li, J.T.1    Bian, Y.J.2    Zang, H.J.3    Li, T.S.4
  • 28
    • 0036098518 scopus 로고    scopus 로고
    • Pinacol coupling of aromatic aldehydes and ketones using aluminum under ultrasound
    • (b) Bian, Y. J.; Li, J. T.; Zang, H. J.; Li, T. S. Pinacol coupling of aromatic aldehydes and ketones using aluminum under ultrasound. Synth. Commun. 2002, 32, 1169;
    • (2002) Synth. Commun. , vol.32 , pp. 1169
    • Bian, Y.J.1    Li, J.T.2    Zang, H.J.3    Li, T.S.4
  • 29
    • 0038044689 scopus 로고    scopus 로고
    • Reductive coupling of aromatic aldehydes using manganese under ultrasound irradiation
    • (c) Li, J. T.; Bian, Y. J.; Liu, S. M.; Li, T. S. Reductive coupling of aromatic aldehydes using manganese under ultrasound irradiation. Chin. J. Org. Chem. 2003, 23, 479.
    • (2003) Chin. J. Org. Chem. , vol.23 , pp. 479
    • Li, J.T.1    Bian, Y.J.2    Liu, S.M.3    Li, T.S.4
  • 30
    • 0242392349 scopus 로고
    • Sonochemical removal of absorbed water and alcohol from magnesium surfaces
    • Sprich, J. D.; Lewandos, G. S. Sonochemical removal of absorbed water and alcohol from magnesium surfaces. Inorg. Chim. Acta. 1983, 76 (4), 241.
    • (1983) Inorg. Chim. Acta. , vol.76 , Issue.4 , pp. 241
    • Sprich, J.D.1    Lewandos, G.S.2
  • 31
    • 0035953031 scopus 로고    scopus 로고
    • Efficient diastereo-selective pinacol coupling reaction of aliphatic and aromatic aldehydes by using newly utilized low valent titanium bromide and iodide species
    • (a) Mukaiyama, T.; Yoshimura, T.; Igarashi, K.; Kagayama, A. Efficient diastereo-selective pinacol coupling reaction of aliphatic and aromatic aldehydes by using newly utilized low valent titanium bromide and iodide species. Tetrahedron. 2001, 57, 2499;
    • (2001) Tetrahedron , vol.57 , pp. 2499
    • Mukaiyama, T.1    Yoshimura, T.2    Igarashi, K.3    Kagayama, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.