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Volumn , Issue , 2009, Pages 163-178

Waste-Minimized Mizoroki-Heck Reactions

Author keywords

Carboxylic anhydrides; Carboxylic esters; Intramolecular oxidative vinylation of indoles; Oxidative arene vinylation using tert butyl hydroperoxide; Rhodium and ruthenium catalysts; Ruthenium catalyzed vinylation; Waste minimized Mizoroki Heck reactions

Indexed keywords


EID: 77950359935     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470716076.ch4     Document Type: Chapter
Times cited : (3)

References (35)
  • 1
    • 0000929187 scopus 로고    scopus 로고
    • Homogeneous catalysis for the production of fine chemicals. Palladium- and nickel-catalyzed aromatic carbon-carbon bond formation
    • Tucker, C.E. and de Vries, J.G. (2002) Homogeneous catalysis for the production of fine chemicals. Palladium- and nickel-catalyzed aromatic carbon-carbon bond formation. Top. Catal., 19, 111-8.
    • (2002) Top. Catal. , vol.19 , pp. 111-118
    • Tucker, C.E.1    De Vries, J.G.2
  • 2
    • 0036589261 scopus 로고    scopus 로고
    • Ru-, Rh-, and Pd-catalyzed C C bond formation involving C H activation and addition on unsaturated substrates: reactions and mechanistic aspects
    • For a review on C H activation chemistry, see
    • For a review on C H activation chemistry, see: Ritlend, V., Sirlin, C. and Pfeffer, M. (2002) Ru-, Rh-, and Pd-catalyzed C C bond formation involving C H activation and addition on unsaturated substrates: reactions and mechanistic aspects. Chem. Rev., 102, 1731-69.
    • (2002) Chem. Rev. , vol.102 , pp. 1731-1769
    • Ritlend, V.1    Sirlin, C.2    Pfeffer, M.3
  • 3
    • 0034249671 scopus 로고    scopus 로고
    • The Heck reaction as a sharpening stone of palladium catalysis
    • Beletskaya, I.P. and Cheprakov, A.V. (2000) The Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev., 100, 3009-66;
    • (2000) Chem. Rev. , vol.100 , pp. 3009-3066
    • Beletskaya, I.P.1    Cheprakov, A.V.2
  • 4
    • 27844611214 scopus 로고    scopus 로고
    • Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: A critical overview. Part 1: the Heck reaction
    • Alonso, F., Beletskaya, I.P. and Yus, M. (2005) Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: A critical overview. Part 1: the Heck reaction. Tetrahedron, 61, 11771-835.
    • (2005) Tetrahedron , vol.61 , pp. 11771-11835
    • Alonso, F.1    Beletskaya, I.P.2    Yus, M.3
  • 5
    • 37049111808 scopus 로고
    • Palladium-catalysed vinylation of organic halides under solid-liquid phase transfer conditions
    • Jeffery, T. (1984) Palladium-catalysed vinylation of organic halides under solid-liquid phase transfer conditions. J. Chem. Soc., Chem. Commun., 1287-8;
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 1287-1288
    • Jeffery, T.1
  • 6
    • 1242338934 scopus 로고    scopus 로고
    • Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle
    • Botella, L. and Najera, C. (2004) Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle. Tetrahedron Lett., 45, 1833-6.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1833-1836
    • Botella, L.1    Najera, C.2
  • 7
    • 20444493628 scopus 로고    scopus 로고
    • Palladium-catalysed carbon carbon bond formation in supercritical carbon dioxide
    • Carroll, M.A. and Holmes, A.B. (1998) Palladium-catalysed carbon carbon bond formation in supercritical carbon dioxide. J. Chem. Soc., Chem. Commun., 1395-6;
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 1395-1396
    • Carroll, M.A.1    Holmes, A.B.2
  • 8
    • 20444496149 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-coupling reactions in supercritical carbon dioxide
    • Morita, D.K., Pesiri, D.R., David, S.A. et al. (1998) Palladium-catalyzed cross-coupling reactions in supercritical carbon dioxide. J. Chem. Soc., Chem. Commun., 1397-8.
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 1397-1398
    • Morita, D.K.1    Pesiri, D.R.2    David, S.A.3
  • 9
    • 0002591690 scopus 로고
    • Aromatic substitution of styrene-palladium chloride complex
    • Moritani, I. and Fujiwara, Y. (1967) Aromatic substitution of styrene-palladium chloride complex. Tetrahedron Lett., 1119-22.
    • (1967) Tetrahedron Lett. , pp. 1119-1122
    • Moritani, I.1    Fujiwara, Y.2
  • 10
    • 0000875742 scopus 로고
    • Aromatic substitution of olefins. VI. Arylation of olefins with palladium(II) acetate
    • Fujiwara, Y., Moritani, I., Danno, S. et al. (1969) Aromatic substitution of olefins. VI. Arylation of olefins with palladium(II) acetate. J. Am. Chem. Soc., 91, 7166-9.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 7166-7169
    • Fujiwara, Y.1    Moritani, I.2    Danno, S.3
  • 11
    • 37049140307 scopus 로고
    • Catalytic coupling of aromatics and olefins by homogeneous palladium(II) compounds under oxygen
    • Shue, R.S. (1971) Catalytic coupling of aromatics and olefins by homogeneous palladium(II) compounds under oxygen. J. Chem. Soc., Chem. Commun., 1510-1.
    • (1971) J. Chem. Soc., Chem. Commun. , pp. 1510-1511
    • Shue, R.S.1
  • 12
    • 4644268281 scopus 로고
    • Pd(II) Cu(II)-catalyzed synthesis of mono- and dialkenyl-substituted five-membered aromatic heterocycles
    • Maruyama, O., Yoshidomi, M., Fujiwara, Y. and Taniguchi, H. (1979) Pd(II) Cu(II)-catalyzed synthesis of mono- and dialkenyl-substituted five-membered aromatic heterocycles. Chem. Lett., 1229-30.
    • (1979) Chem. Lett. , pp. 1229-1230
    • Maruyama, O.1    Yoshidomi, M.2    Fujiwara, Y.3    Taniguchi, H.4
  • 13
    • 0042531833 scopus 로고    scopus 로고
    • Toward waste-free production of Heck products with a catalytic palladium system under oxygen
    • Dams, M., de Vos, D.E., Celen, S. and Jacobs, P.A. (2003) Toward waste-free production of Heck products with a catalytic palladium system under oxygen. Angew. Chem. Int. Ed., 42, 3512-5.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3512-3515
    • Dams, M.1    De Vos, D.E.2    Celen, S.3    Jacobs, P.A.4
  • 14
    • 0001400640 scopus 로고
    • Activation of aromatic carbon-hydrogen bonds by palladium(II) acetate-dialkyl sulfide systems. Formation and characterization of novel diphenyltripalladium(II) complexes
    • Fuchita, Y., Hiraki, K., Kamogawa, Y. et al. (1989) Activation of aromatic carbon-hydrogen bonds by palladium(II) acetate-dialkyl sulfide systems. Formation and characterization of novel diphenyltripalladium(II) complexes. Bull. Chem. Soc. Jpn., 62, 1081-5.
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 1081-1085
    • Fuchita, Y.1    Hiraki, K.2    Kamogawa, Y.3
  • 15
    • 0037433243 scopus 로고    scopus 로고
    • Direct coupling of benzene with olefin catalyzed by Pd(OAc)2 combined with heteropolyoxometalate under dioxygen
    • Yokota, T., Tani, M., Sakaguchi, S. and Ishii, Y. (2003) Direct coupling of benzene with olefin catalyzed by Pd(OAc)2 combined with heteropolyoxometalate under dioxygen. J. Am. Chem. Soc., 125, 1476-7;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1476-1477
    • Yokota, T.1    Tani, M.2    Sakaguchi, S.3    Ishii, Y.4
  • 16
    • 1242352467 scopus 로고    scopus 로고
    • Pd(OAc)2-catalyzed oxidative coupling reaction of benzenes with olefins in the presence of molybdovanadophosphoric acid under atmospheric dioxygen and air
    • Tani, M., Sakaguchi, S. and Ishii, Y. (2004) Pd(OAc)2-catalyzed oxidative coupling reaction of benzenes with olefins in the presence of molybdovanadophosphoric acid under atmospheric dioxygen and air. J. Org. Chem., 69, 1221-6.
    • (2004) J. Org. Chem. , vol.69 , pp. 1221-1226
    • Tani, M.1    Sakaguchi, S.2    Ishii, Y.3
  • 17
    • 0000954930 scopus 로고
    • Palladium-catalyzed oxidative coupling of aromatic compounds with olefins using tert-butyl perbenzoate as a hydrogen accepter
    • Tsuji, J. and Nagashima, H. (1984) Palladium-catalyzed oxidative coupling of aromatic compounds with olefins using tert-butyl perbenzoate as a hydrogen accepter. Tetrahedron, 40, 2699-702.
    • (1984) Tetrahedron , vol.40 , pp. 2699-2702
    • Tsuji, J.1    Nagashima, H.2
  • 18
    • 0000185795 scopus 로고    scopus 로고
    • Highly efficient Pd-catalyzed coupling of arenes with olefins in the presence of tert-butyl hydroperoxide as oxidant
    • Jia, C., Lu, W., Kitamura, T. and Fujiwara, Y. (1999) Highly efficient Pd-catalyzed coupling of arenes with olefins in the presence of tert-butyl hydroperoxide as oxidant. Org. Lett., 1, 2097-100.
    • (1999) Org. Lett. , vol.1 , pp. 2097-2100
    • Jia, C.1    Lu, W.2    Kitamura, T.3    Fujiwara, Y.4
  • 19
    • 10044267678 scopus 로고    scopus 로고
    • Direct oxidative Heck cyclizations: intramolecular Fujiwara-Moritani arylations for the synthesis of functionalized benzofurans and dihydrobenzofurans
    • Zhang, H., Ferreira, E.M. and Stoltz, B.M. (2004) Direct oxidative Heck cyclizations: intramolecular Fujiwara-Moritani arylations for the synthesis of functionalized benzofurans and dihydrobenzofurans. Angew. Chem. Int. Ed., 43, 6144-8.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 6144-6148
    • Zhang, H.1    Ferreira, E.M.2    Stoltz, B.M.3
  • 20
    • 0041624424 scopus 로고    scopus 로고
    • Catalytic C H bond functionalization with palladium(II): aerobic oxidative annulations of indoles
    • Ferreira, E.M. and Stoltz, B.M. (2003) Catalytic C H bond functionalization with palladium(II): aerobic oxidative annulations of indoles. J. Am. Chem. Soc., 125, 9578-9.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 9578-9579
    • Ferreira, E.M.1    Stoltz, B.M.2
  • 21
    • 0037181051 scopus 로고    scopus 로고
    • Selective Pd-catalyzed oxidative coupling of anilides with olefins through C H bond activation at room temperature
    • Boele, M.D.K., van Strijdonck, G.P.F., de Vries, A.H.M. et al. (2002) Selective Pd-catalyzed oxidative coupling of anilides with olefins through C H bond activation at room temperature. J. Am. Chem. Soc., 124, 1586-7.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1586-1587
    • Boele, M.D.K.1    Van Strijdonck, G.P.F.2    De Vries, A.H.M.3
  • 22
    • 29144481961 scopus 로고    scopus 로고
    • Pd-catalyzed ortho-selective oxidative coupling of halogenated acetanilides with acrylates
    • Lee, G.T., Jiang, X., Prasad, K. et al. (2005) Pd-catalyzed ortho-selective oxidative coupling of halogenated acetanilides with acrylates. Adv. Synth. Catal., 347, 1921-4.
    • (2005) Adv. Synth. Catal. , vol.347 , pp. 1921-1924
    • Lee, G.T.1    Jiang, X.2    Prasad, K.3
  • 23
    • 0001329322 scopus 로고
    • Reactions of ethylene and benzenes catalyzed by rhodium carbonyls under carbon monoxide. The formation of styrenes and 3-pentanone
    • Hong, P. and Yamazaki, H. (1979) Reactions of ethylene and benzenes catalyzed by rhodium carbonyls under carbon monoxide. The formation of styrenes and 3-pentanone. Chem. Lett., 1335-6;
    • (1979) Chem. Lett. , pp. 1335-1336
    • Hong, P.1    Yamazaki, H.2
  • 24
    • 0021510248 scopus 로고
    • Rhodium carbonyl-catalyzed activation of carbon-hydrogen bonds for application in organic synthesis: V. Phenylation of olefins with benzenes
    • Hong, P. and Yamazaki, H. (1984) Rhodium carbonyl-catalyzed activation of carbon-hydrogen bonds for application in organic synthesis: V. Phenylation of olefins with benzenes. J. Mol. Catal., 26, 297-311.
    • (1984) J. Mol. Catal. , vol.26 , pp. 297-311
    • Hong, P.1    Yamazaki, H.2
  • 25
    • 0037885777 scopus 로고
    • C C double bond insertion in catalytic C H activation. Dehydrogenative cross coupling of arenes with olefins
    • Sasaki, K., Sakakura, T., Tokunaga, Y. et al. (1988) C C double bond insertion in catalytic C H activation. Dehydrogenative cross coupling of arenes with olefins. Chem. Lett., 685-8.
    • (1988) Chem. Lett. , pp. 685-688
    • Sasaki, K.1    Sakakura, T.2    Tokunaga, Y.3
  • 26
    • 0034339977 scopus 로고    scopus 로고
    • Oxidative arylation of ethylene with benzene to produce styrene
    • Matsumoto, T. and Yoshida, H. (2000) Oxidative arylation of ethylene with benzene to produce styrene. Chem. Lett., 29, 1064-5.
    • (2000) Chem. Lett. , vol.29 , pp. 1064-1065
    • Matsumoto, T.1    Yoshida, H.2
  • 27
    • 0034677867 scopus 로고    scopus 로고
    • Efficient activation of aromatic C H bonds for addition to C C multiple bonds
    • The hydroarylation of alkynes, which has emerged as a powerful alternative to the oxidative arylation of alkene, is not discussed in this chapter as it is not a true Heck alkenylation
    • The hydroarylation of alkynes, which has emerged as a powerful alternative to the oxidative arylation of alkene, is not discussed in this chapter as it is not a true Heck alkenylation. Jia, C., Piao, D., Oyamada, J. et al. (2000) Efficient activation of aromatic C H bonds for addition to C C multiple bonds. Science, 287, 1992-5.
    • (2000) Science , vol.287 , pp. 1992-1995
    • Jia, C.1    Piao, D.2    Oyamada, J.3
  • 28
    • 0035900977 scopus 로고    scopus 로고
    • Ru-catalyzed oxidative coupling of arenes with olefins using O2
    • Weissman, H., Song, X. and Milstein, D. (2001) Ru-catalyzed oxidative coupling of arenes with olefins using O2. J. Am. Chem. Soc., 123, 337-8.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 337-338
    • Weissman, H.1    Song, X.2    Milstein, D.3
  • 29
    • 12344295406 scopus 로고    scopus 로고
    • Rhodium-catalyzed coupling reaction of aroyl chlorides with alkenes
    • Sugihara, T., Satoh, T., Miura, M. and Nomura, M. (2004) Rhodium-catalyzed coupling reaction of aroyl chlorides with alkenes. Adv. Synth. Catal., 346, 1765-72.
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1765-1772
    • Sugihara, T.1    Satoh, T.2    Miura, M.3    Nomura, M.4
  • 30
    • 27644482173 scopus 로고    scopus 로고
    • Mizoroki-Heck type arylation of alkenes using aroyl chlorides under base-free conditions
    • Sugihara, T., Satoh, T. and Miura, M. (2005) Mizoroki-Heck type arylation of alkenes using aroyl chlorides under base-free conditions. Tetrahedron Lett., 46, 8269-71.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 8269-8271
    • Sugihara, T.1    Satoh, T.2    Miura, M.3
  • 31
    • 0031925015 scopus 로고    scopus 로고
    • Heck reactions without salt formation: aromatic carboxylic anhydrides as arylating agents
    • Stephan, M.S., Teunissen, A.J.J.M., Verzijl, G.K.M. and de Vries, J.G. (1998) Heck reactions without salt formation: aromatic carboxylic anhydrides as arylating agents. Angew. Chem. Int. Ed., 37, 662-4.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 662-664
    • Stephan, M.S.1    Teunissen, A.J.J.M.2    Verzijl, G.K.M.3    De Vries, J.G.4
  • 32
    • 0036403388 scopus 로고    scopus 로고
    • Pd-catalyzed decarbonylative Heck olefination of aromatic carboxylic acids activated in situ with di-tert-butyl dicarbonate
    • Goossen, L.J., Paetzold, J. and Winkel, L. (2002) Pd-catalyzed decarbonylative Heck olefination of aromatic carboxylic acids activated in situ with di-tert-butyl dicarbonate. Synlett, 1721-3.
    • (2002) Synlett , pp. 1721-1723
    • Goossen, L.J.1    Paetzold, J.2    Winkel, L.3
  • 33
    • 0037006837 scopus 로고    scopus 로고
    • Pd-catalyzed decarbonylative olefination of aryl esters: towards a waste-free Heck reaction
    • Goossen, L.J. and Paetzold, J. (2002) Pd-catalyzed decarbonylative olefination of aryl esters: towards a waste-free Heck reaction. Angew. Chem. Int. Ed., 41, 1237-41.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1237-1241
    • Goossen, L.J.1    Paetzold, J.2
  • 34
    • 0012666798 scopus 로고    scopus 로고
    • Utilization of an industrial feedstock without separation. Ruthenium-catalysed hydrocarboxylation of propadiene and propyne
    • Bruneau, C., Neveux-Duflos, M. and Dixneuf, P.H. (1999) Utilization of an industrial feedstock without separation. Ruthenium-catalysed hydrocarboxylation of propadiene and propyne. Green Chem., 1, 183-5.
    • (1999) Green Chem. , vol.1 , pp. 183-185
    • Bruneau, C.1    Neveux-Duflos, M.2    Dixneuf, P.H.3
  • 35
    • 4544255784 scopus 로고    scopus 로고
    • Decarbonylative Heck olefination of enol esters: salt-free and environmentally friendly access to vinyl arenes
    • Goossen, L.J. and Paetzold, J. (2004) Decarbonylative Heck olefination of enol esters: salt-free and environmentally friendly access to vinyl arenes. Angew. Chem. Int. Ed., 43, 1095-8.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1095-1098
    • Goossen, L.J.1    Paetzold, J.2


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