메뉴 건너뛰기




Volumn 36, Issue 19, 2006, Pages 2851-2857

Novel C-C bond cleavage from arylacetonitriles in alcohols to aryl carboxylic esters using potassium iodide and catalytic amount of samarium

Author keywords

Aryl carboxylic ester; Arylacetonitrile; C C bond cleavage; Potassium iodide; Samarium

Indexed keywords

ACETONITRILE DERIVATIVE; ALCOHOL DERIVATIVE; ESTER; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM IODIDE; SAMARIUM;

EID: 33750069726     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600770680     Document Type: Article
Times cited : (9)

References (27)
  • 1
    • 33847086035 scopus 로고
    • Divalent lanthanide derivatives in organic synthesis, 1: Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents
    • Girard, P.; Namy, J. L.; Kangan, H. B. Divalent lanthanide derivatives in organic synthesis, 1: Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents. J. Am. Chem. Soc. 1980, 102, 2693-2698.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2693-2698
    • Girard, P.1    Namy, J.L.2    Kangan, H.B.3
  • 2
    • 0010077452 scopus 로고
    • Application of lanthanide reagents in organic synthesis
    • Molander, G. A. Application of lanthanide reagents in organic synthesis. Chem. Rev. 1992, 92, 29-68.
    • (1992) Chem. Rev. , vol.92 , pp. 29-68
    • Molander, G.A.1
  • 3
    • 2142715741 scopus 로고    scopus 로고
    • Sequencing reaction with samarium(II) iodide
    • Molander, G. A.; Harris, C. R. Sequencing reaction with samarium(II) iodide. Chem. Rev. 1996, 96, 307-338.
    • (1996) Chem. Rev. , vol.96 , pp. 307-338
    • Molander, G.A.1    Harris, C.R.2
  • 4
    • 0041353712 scopus 로고    scopus 로고
    • Application of samarium reagents in organic synthesis
    • Yu, M. X.; Zhang, Y. M.; Bao, W. L. Application of samarium reagents in organic synthesis. Chin. J. Chem. 1999, 17, 4-15.
    • (1999) Chin. J. Chem. , vol.17 , pp. 4-15
    • Yu, M.X.1    Zhang, Y.M.2    Bao, W.L.3
  • 5
    • 33750063727 scopus 로고    scopus 로고
    • New progress in the application of samarium reagent to organic synthesis
    • Liu, Y. J.; Zhang, Y. M. New progress in the application of samarium reagent to organic synthesis. Chin. Actc. Chimica Sinica 2005, 63 (5), 341-351.
    • (2005) Chin. Actc. Chimica Sinica , vol.63 , Issue.5 , pp. 341-351
    • Liu, Y.J.1    Zhang, Y.M.2
  • 6
    • 0037423344 scopus 로고    scopus 로고
    • Sequential elimination-cyclo propanation reactions promoted by samarium: Highly diastereoselective synthesis of cyclopropylamindes
    • Concellon, J. M.; Rodriguez-Solla, H.; Llavona, R. Sequential elimination-cyclo propanation reactions promoted by samarium: Highly diastereoselective synthesis of cyclopropylamindes. J. Org. Chem. 2003, 68, 1132-1133.
    • (2003) J. Org. Chem. , vol.68 , pp. 1132-1133
    • Concellon, J.M.1    Rodriguez-Solla, H.2    Llavona, R.3
  • 7
    • 0035847217 scopus 로고    scopus 로고
    • Reduction and coupling reactions of carbonyl compounds using samarium metal in aqueous media
    • Talukdar, S.; Fang, J. M. Reduction and coupling reactions of carbonyl compounds using samarium metal in aqueous media. J. Org. Chem. 2001, 66, 330-333.
    • (2001) J. Org. Chem. , vol.66 , pp. 330-333
    • Talukdar, S.1    Fang, J.M.2
  • 9
    • 0034694729 scopus 로고    scopus 로고
    • Selective side chain introduction onto small peptide mediated by samarium diiodide: A potential route to peptide libraries
    • Ricci, M.; Blakskjaer, P.; Skrydstrup, T. Selective side chain introduction onto small peptide mediated by samarium diiodide: A potential route to peptide libraries. J. Am. Chem. Soc. 2000, 122, 12413-12421.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12413-12421
    • Ricci, M.1    Blakskjaer, P.2    Skrydstrup, T.3
  • 10
    • 0037427297 scopus 로고    scopus 로고
    • 2 reduced thioesters as synthons of unstable acyl radicals: Direct synthesis of potential protease inhibitors via intermolecular radical addition
    • 2 reduced thioesters as synthons of unstable acyl radicals: Direct synthesis of potential protease inhibitors via intermolecular radical addition. J. Am. Chem. Soc. 2003, 125, 4030-4031.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4030-4031
    • Blakskjaer, P.1    Hoj, B.2    Riber, D.3    Skrydstrup, T.4
  • 11
    • 0037463460 scopus 로고    scopus 로고
    • Synthesis of (E)-alpha, beta-unsaturated ketones with total or high diastereoselectivity by using samarium diiodide or triiodide
    • Concellon, J. M.; Huerta, M. Synthesis of (E)-alpha, beta-unsaturated ketones with total or high diastereoselectivity by using samarium diiodide or triiodide. Tetrahedron Lett. 2003, 44, 1931-1934.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1931-1934
    • Concellon, J.M.1    Huerta, M.2
  • 13
    • 0042650033 scopus 로고    scopus 로고
    • Facile oxidation of aldehydes to acids and esters with oxone
    • Travis, B. R.; Sivakumer, M.; Hollist, G. O.; Borhan, B. Facile oxidation of aldehydes to acids and esters with oxone. Org. Lett. 2003, 5 (7), 1031-1034.
    • (2003) Org. Lett. , vol.5 , Issue.7 , pp. 1031-1034
    • Travis, B.R.1    Sivakumer, M.2    Hollist, G.O.3    Borhan, B.4
  • 14
    • 0037419411 scopus 로고    scopus 로고
    • Peroxovanadium-catalyzed oxidative esterification of aldehydes
    • Gopinath, R.; Barkakaty, B.; Talukdar, B.; Patel, B. K. Peroxovanadium-catalyzed oxidative esterification of aldehydes. J. Org. Chem. 2003, 68, 2944-2947.
    • (2003) J. Org. Chem. , vol.68 , pp. 2944-2947
    • Gopinath, R.1    Barkakaty, B.2    Talukdar, B.3    Patel, B.K.4
  • 15
    • 0037040685 scopus 로고    scopus 로고
    • Novel C-C bond cleavage under mild, neutral conditions: Conversion of electron-deficient aryl alkyl ketones to aryl carboxylic esters
    • Zhang, N.; Vozzolo, J. Novel C-C bond cleavage under mild, neutral conditions: Conversion of electron-deficient aryl alkyl ketones to aryl carboxylic esters. J. Org. Chem. 2002, 67, 1703-1704.
    • (2002) J. Org. Chem. , vol.67 , pp. 1703-1704
    • Zhang, N.1    Vozzolo, J.2
  • 16
    • 0037458802 scopus 로고    scopus 로고
    • Dimethylmalonyltrialkylphosphoranes: New general reagents for esterification reactions allowing controlled inversion or retention of configuration on chiral alcohols
    • McNulty, J.; Capretta, A.; Laritchev, V.; Dyck, J.; Robertson, A. J. Dimethylmalonyltrialkylphosphoranes: New general reagents for esterification reactions allowing controlled inversion or retention of configuration on chiral alcohols. J. Org. Chem. 2003, 68, 1597-1600.
    • (2003) J. Org. Chem. , vol.68 , pp. 1597-1600
    • McNulty, J.1    Capretta, A.2    Laritchev, V.3    Dyck, J.4    Robertson, A.J.5
  • 17
    • 1542476427 scopus 로고
    • Esterification of carboxylic acids with trialkyloxonium salts
    • Raber, D. J.; Gariano, P. Jr.; Brod, A. O. Esterification of carboxylic acids with trialkyloxonium salts. J. Org. Chem. 1979, 44, 1149-1154.
    • (1979) J. Org. Chem. , vol.44 , pp. 1149-1154
    • Raber, D.J.1    Gariano Jr., P.2    Brod, A.O.3
  • 18
    • 84989446534 scopus 로고
    • A simple procedure for the esterification of carboxylic acids
    • Brook, M. A.; Chan, T. H. A simple procedure for the esterification of carboxylic acids. Synthesis 1983, 3, 201-203.
    • (1983) Synthesis , vol.3 , pp. 201-203
    • Brook, M.A.1    Chan, T.H.2
  • 20
    • 85083212443 scopus 로고
    • Solid-liquid phase-transfer catalysis without added solvent: A simple, efficient, and inexpensive synthesis of aromatic carboxylic esters by alkylation of potassium carboxylates
    • Barry, J.; Bram, G.; Decodts, G.; Loupy, A.; Orange, C.; Petit, A.; Sansoulet, J. Solid-liquid phase-transfer catalysis without added solvent: A simple, efficient, and inexpensive synthesis of aromatic carboxylic esters by alkylation of potassium carboxylates. Synthesis 1985, 1, 40-45.
    • (1985) Synthesis , vol.1 , pp. 40-45
    • Barry, J.1    Bram, G.2    Decodts, G.3    Loupy, A.4    Orange, C.5    Petit, A.6    Sansoulet, J.7
  • 21
    • 0041315732 scopus 로고    scopus 로고
    • Efficient method for the preparation of carboxylic acid alkyl esters or alkyl phenyl ethers by a new type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and alkoxydiphenylphosphines
    • Shintou, T.; Kikuchi, W.; Mukaiyama, T. Efficient method for the preparation of carboxylic acid alkyl esters or alkyl phenyl ethers by a new type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and alkoxydiphenylphosphines. Bull. Chem. Soc. Japan 2003, 76, 1645-1667.
    • (2003) Bull. Chem. Soc. Japan , vol.76 , pp. 1645-1667
    • Shintou, T.1    Kikuchi, W.2    Mukaiyama, T.3
  • 22
    • 3843111136 scopus 로고    scopus 로고
    • Novel polymer-supported coupling/dehydrating reagents for use in organic synthesis
    • Fairfull-Smith, K. E.; Jenkins, I. D.; Loughlin, W. A. Novel polymer-supported coupling/dehydrating reagents for use in organic synthesis. Org. Biomol. Chem. 2004, 2, 1979-1986.
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 1979-1986
    • Fairfull-Smith, K.E.1    Jenkins, I.D.2    Loughlin, W.A.3
  • 23
    • 0036173259 scopus 로고    scopus 로고
    • An efficient and simple procedure for preparation of esters and anhydrides from acid chlorides in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) under solvent-free conditions
    • Hajipour, A. R.; Mazloumi, G. H. An efficient and simple procedure for preparation of esters and anhydrides from acid chlorides in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) under solvent-free conditions. Synth. Commun. 2002, 32, 23-30.
    • (2002) Synth. Commun. , vol.32 , pp. 23-30
    • Hajipour, A.R.1    Mazloumi, G.H.2
  • 24
    • 85077537430 scopus 로고
    • Synthetic methods and reactions: Sulfuryl chloride fluoride-mediated esterification of carboxylic acids with alcohols
    • Olah, G. A.; Narang, S. C.; Garcia-Luna, A. Synthetic methods and reactions: Sulfuryl chloride fluoride-mediated esterification of carboxylic acids with alcohols. Synthesis 1981, 10, 790-791.
    • (1981) Synthesis , vol.10 , pp. 790-791
    • Olah, G.A.1    Narang, S.C.2    Garcia-Luna, A.3
  • 25
    • 0009701770 scopus 로고
    • Mechanism of the reaction of lithium reagents with esters
    • Al-Aseer, M. A.; Allison, B. D.; Smith, S. G. Mechanism of the reaction of lithium reagents with esters. J. Org. Chem. 1985, 50, 2715-2719.
    • (1985) J. Org. Chem. , vol.50 , pp. 2715-2719
    • Al-Aseer, M.A.1    Allison, B.D.2    Smith, S.G.3
  • 26
    • 7044226222 scopus 로고    scopus 로고
    • Guanidinium nitrate: A novel reagent for aryl nitrations
    • Ramana, M. M. V.; Malik, S. S.; Parihar, J. A. Guanidinium nitrate: A novel reagent for aryl nitrations. Tetrahedron Lett. 2004, 45, 8681-8683.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 8681-8683
    • Ramana, M.M.V.1    Malik, S.S.2    Parihar, J.A.3
  • 27
    • 33750069805 scopus 로고
    • Preparation of dimethyl 4,4′-azoxydibenzoate: An anomalous benzoin condensation reaction
    • Waldrep, D.; Yager, B. J. Preparation of dimethyl 4,4′- azoxydibenzoate: An anomalous benzoin condensation reaction. Texas J. Sci. 1976, 27, 397-399.
    • (1976) Texas J. Sci. , vol.27 , pp. 397-399
    • Waldrep, D.1    Yager, B.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.