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Volumn , Issue 5, 2008, Pages 629-644

On inventing catalytic reactions via ruthena- or rhodacyclic intermediates for atom economy

Author keywords

C C bond cleavage; Catalyst; Cocyclization; Rhodium; Ruthenium

Indexed keywords

2 PYRIDONE DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; CARBON MONOXIDE; ETHYLENE; HYDROQUINONE; ISOCYANATE; RHODIUM; RUTHENIUM; STYRENE DERIVATIVE;

EID: 41349097340     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042807     Document Type: Review
Times cited : (27)

References (296)
  • 23
    • 41349083928 scopus 로고    scopus 로고
    • In Alkene Metathesis in Organic Synthesis; Fürstner, A, Ed, Springer: Berlin, 1998
    • (b) In Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998.
  • 29
    • 0002648396 scopus 로고
    • Trost, B. M, Fleming, I, Paquette, L. A, Eds, Pergamon: Oxford
    • Baldwin, J. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991, 63-84.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 63-84
    • Baldwin, J.E.1
  • 30
    • 0000167986 scopus 로고
    • Trost, B. M, Fleming, I, Paquette, L. A, Eds, Pergamon: Oxford
    • Crimmins, M. T. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991, 123-150.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 123-150
    • Crimmins, M.T.1
  • 39
    • 0003779363 scopus 로고    scopus 로고
    • 2nd ed, Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim, Chap. 3.13, 619-632
    • (a) Strübing, D.; Beller, M. In Transition Metals for Organic Synthesis, 2nd ed., Vol. 1; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004, Chap. 3.13, 619-632.
    • (2004) Transition Metals for Organic Synthesis , vol.1
    • Strübing, D.1    Beller, M.2
  • 40
    • 4644324093 scopus 로고    scopus 로고
    • For recent reviews, see: b
    • For recent reviews, see: (b) Boñaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
    • (2004) Tetrahedron , vol.60 , pp. 9795
    • Boñaga, L.V.R.1    Krafft, M.E.2
  • 45
    • 0000687565 scopus 로고    scopus 로고
    • Ruthenium-catalyzed Pauson-Khand-type reaction under similar reaction conditions has been independently reported by Murai and co-workers: Morimoto, T, Chatani, N, Fukumoto, Y, Murai, S. J. Org. Chem. 1997, 62, 3762
    • (a) Ruthenium-catalyzed Pauson-Khand-type reaction under similar reaction conditions has been independently reported by Murai and co-workers: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
  • 46
    • 41349100660 scopus 로고    scopus 로고
    • In the Murai's reaction no cyclopentenones (5e and 5f) were obtained from these substrates
    • (b) In the Murai's reaction no cyclopentenones (5e and 5f) were obtained from these substrates.
  • 47
    • 0000595091 scopus 로고    scopus 로고
    • Trimethylsilyl-substituted enyne 4d gave the desilylated product in the titanocene-catalyzed reaction of enynes with silylcyanide: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593.
    • Trimethylsilyl-substituted enyne 4d gave the desilylated product in the titanocene-catalyzed reaction of enynes with silylcyanide: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593.
  • 53
    • 0038662179 scopus 로고    scopus 로고
    • For Co: (a) Macomber, D. W.; Verma, A. G.; Rogers, R. D. Organometallics 1988, 7, 1241.
    • For Co: (a) Macomber, D. W.; Verma, A. G.; Rogers, R. D. Organometallics 1988, 7, 1241.
  • 58
    • 12044255581 scopus 로고    scopus 로고
    • For Ti: (f) Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1993, 115, 1581.
    • For Ti: (f) Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1993, 115, 1581.
  • 60
    • 0032567406 scopus 로고    scopus 로고
    • For Ru: (h) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610.
    • For Ru: (h) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610.
  • 63
    • 37049067977 scopus 로고    scopus 로고
    • For Rh: (k) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1365.
    • For Rh: (k) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1365.
  • 64
    • 0000182458 scopus 로고    scopus 로고
    • For Ni: (l) Chalk, A. J. J. Am. Chem. Soc. 1972, 94, 5928.
    • For Ni: (l) Chalk, A. J. J. Am. Chem. Soc. 1972, 94, 5928.
  • 66
    • 0032547249 scopus 로고    scopus 로고
    • For direct observation of cobaltacyclopentadienes and their related reactions in terms of the reaction mechanism for alkyne cyclotrimerization, see: (a) Diercks, R, Eaton, B. E, Gürtzgen, S, Jalisatgi, S, Matzger, A. J, Radde, R. H, Vollhardt, K. P. C. J. Am. Chem. Soc. 1998, 120, 8247. Recently, pathways involving cascades of metathesis steps in ruthenium-catalyzed conversion of triynes to benzene derivatives have also been described
    • For direct observation of cobaltacyclopentadienes and their related reactions in terms of the reaction mechanism for alkyne cyclotrimerization, see: (a) Diercks, R.; Eaton, B. E.; Gürtzgen, S.; Jalisatgi, S.; Matzger, A. J.; Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1998, 120, 8247. Recently, pathways involving cascades of metathesis steps in ruthenium-catalyzed conversion of triynes to benzene derivatives have also been described.
  • 74
    • 0000110406 scopus 로고    scopus 로고
    • Cf The reactions of ruthenacyclopentadiene with heterocumulenes, see: b
    • Cf The reactions of ruthenacyclopentadiene with heterocumulenes, see: (b) Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117.
    • (2001) Org. Lett , vol.3 , pp. 2117
    • Yamamoto, Y.1    Takagishi, H.2    Itoh, K.3
  • 81
    • 0000711103 scopus 로고    scopus 로고
    • For thermal and Lewis acid mediated enyne-yne [4+2] cycloaddition, see: (a) Danheiser, R. L.; Gould, A. E.; Fernández de la Predilla, R.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514.
    • For thermal and Lewis acid mediated enyne-yne [4+2] cycloaddition, see: (a) Danheiser, R. L.; Gould, A. E.; Fernández de la Predilla, R.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514.
  • 83
    • 0033553988 scopus 로고    scopus 로고
    • For palladium-catalyzed [4+2] cross-benzannulation of conjugated enynes with diynes, see: (c) Gevorgyan, V.; Takeda, A.; Homma, M.; Sadoyori, N.; Radhakrishnan, U.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 6391; and references therein.
    • For palladium-catalyzed [4+2] cross-benzannulation of conjugated enynes with diynes, see: (c) Gevorgyan, V.; Takeda, A.; Homma, M.; Sadoyori, N.; Radhakrishnan, U.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 6391; and references therein.
  • 93
    • 0001334715 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • (a) Schore, N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 1037-1064.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037-1064
    • Schore, N.E.1
  • 94
    • 0000134376 scopus 로고
    • Hegedus, L. S, Abel, E. W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon Press: Oxford
    • (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II, Vol. 12; Hegedus, L. S.; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995, 741-770.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 741-770
    • Grotjahn, D.B.1
  • 162
    • 0041378064 scopus 로고    scopus 로고
    • and references therein
    • (a) RajanBabu, T. V. Chem. Rev. 2003, 103, 2845; and references therein.
    • (2003) Chem. Rev , vol.103 , pp. 2845
    • RajanBabu, T.V.1
  • 172
    • 4444344478 scopus 로고    scopus 로고
    • Ruthenium-catalyzed head-to-tail dimerization of styrenes to 1,3-diaryl-1-butenes has recently been reported: Higashimura, M.; Imamura, K.; Yokogawa, Y.; Sakakibara, T. Chem. Lett. 2004, 33, 728.
    • Ruthenium-catalyzed head-to-tail dimerization of styrenes to 1,3-diaryl-1-butenes has recently been reported: Higashimura, M.; Imamura, K.; Yokogawa, Y.; Sakakibara, T. Chem. Lett. 2004, 33, 728.
  • 173
    • 27644535373 scopus 로고    scopus 로고
    • 1,4-Diaryl-1-butenes are an important starting material for the synthesis of aryltetralins as well as a key intermediate for the construction of eight-membered-ring systems such as 2,2′-cyclolignans. (a) Hajra, S.; Maji, B.; Karmakar, A. Tetrahedron Lett. 2005, 46, 8599.
    • 1,4-Diaryl-1-butenes are an important starting material for the synthesis of aryltetralins as well as a key intermediate for the construction of eight-membered-ring systems such as 2,2′-cyclolignans. (a) Hajra, S.; Maji, B.; Karmakar, A. Tetrahedron Lett. 2005, 46, 8599.
  • 176
    • 0034801474 scopus 로고    scopus 로고
    • The formation of ruthenacyclopentane was proposed in ruthenium-catalyzed cyclization of 1,6-dienes. Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372.
    • The formation of ruthenacyclopentane was proposed in ruthenium-catalyzed cyclization of 1,6-dienes. Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372.
  • 182
    • 0000735150 scopus 로고    scopus 로고
    • A theoretical study on σ-bond metathesis of Pd(II)-Me with MeOH has been reported: Milet, A.; Dedieu, A.; Kapteijn, G.; van Koten, G. Inorg. Chem. 1997, 36, 3223.
    • A theoretical study on σ-bond metathesis of Pd(II)-Me with MeOH has been reported: Milet, A.; Dedieu, A.; Kapteijn, G.; van Koten, G. Inorg. Chem. 1997, 36, 3223.
  • 197
    • 41349115878 scopus 로고    scopus 로고
    • Squaric acid is also a quite attractive raw material from both synthetic and industrial perspectives: West, R. In Oxocarbons; Academic Press: New York, 1980
    • Squaric acid is also a quite attractive raw material from both synthetic and industrial perspectives: West, R. In Oxocarbons; Academic Press: New York, 1980.
  • 201
    • 0002975857 scopus 로고    scopus 로고
    • 3 is initially inserted into cyclobutenediones in an unsymmetrical fashion to give rhodacyclopentenedione as a kinetic product, see: Liebeskind, L. S.; Baysdon, S. L.; South, M. S.; Blount, J. F. J. Organomet. Chem. 1980, 202, C73.
    • 3 is initially inserted into cyclobutenediones in an unsymmetrical fashion to give rhodacyclopentenedione as a kinetic product, see: Liebeskind, L. S.; Baysdon, S. L.; South, M. S.; Blount, J. F. J. Organomet. Chem. 1980, 202, C73.
  • 207
    • 0001332192 scopus 로고    scopus 로고
    • Coordination effect of an oxygen atom leading to C-H bond activation has been reported. (a) McGuiggan, M. F.; Pignolet, L. H. Inorg. Chem. 1982, 21, 2523.
    • Coordination effect of an oxygen atom leading to C-H bond activation has been reported. (a) McGuiggan, M. F.; Pignolet, L. H. Inorg. Chem. 1982, 21, 2523.
  • 211
    • 0000995098 scopus 로고
    • For a review, see: a
    • For a review, see: (a) Potts, K. T.; Baum, J. S. Chem. Rev. 1974, 74, 189.
    • (1974) Chem. Rev , vol.74 , pp. 189
    • Potts, K.T.1    Baum, J.S.2
  • 214
    • 0003676525 scopus 로고    scopus 로고
    • 4th ed, de Meijere, A, Ed, Thieme: Stuttgart, Chap. 5, 2983-3078
    • (d) Yoshida, Z.; Konishi, H. In Houben-Weyl: Methods of Organic Chemistry, 4th ed., Vol. E17d; de Meijere, A., Ed.; Thieme: Stuttgart, 1997, Chap. 5, 2983-3078.
    • (1997) Houben-Weyl: Methods of Organic Chemistry , vol.E17d
    • Yoshida, Z.1    Konishi, H.2
  • 222
    • 0034681527 scopus 로고    scopus 로고
    • Gade, L. H.; Memmler, H.; Kauper, U.; Schneider, A.; Fabre, S.; Bezougli, I.; Lutz, M.; G alka, C.; Scowen, I. J.; McPartlin, M. Chem. Eur. J. 2000, 6, 692.
    • (b) Gade, L. H.; Memmler, H.; Kauper, U.; Schneider, A.; Fabre, S.; Bezougli, I.; Lutz, M.; G alka, C.; Scowen, I. J.; McPartlin, M. Chem. Eur. J. 2000, 6, 692.
  • 234
    • 41349113758 scopus 로고    scopus 로고
    • Shing, T. K. M. In Houben-Weyl: Methods of Organic Chemistry, 4th ed., E17f; de Meijere, A., Ed.; Thieme: Stuttgart, 1997, Chap. 8B, 898-913.
    • (b) Shing, T. K. M. In Houben-Weyl: Methods of Organic Chemistry, 4th ed., Vol. E17f; de Meijere, A., Ed.; Thieme: Stuttgart, 1997, Chap. 8B, 898-913.
  • 239
    • 0001173186 scopus 로고    scopus 로고
    • A thermal reaction of cyclobutenones with activated alkynes to phenols via a vinylketene intermediate has also been reported, a Danheiser, R. L, Gee, S. K. J. Org. Chem. 1984, 49, 1672
    • A thermal reaction of cyclobutenones with activated alkynes to phenols via a vinylketene intermediate has also been reported. (a) Danheiser, R. L.; Gee, S. K. J. Org. Chem. 1984, 49, 1672.
  • 244
    • 0026530969 scopus 로고    scopus 로고
    • Although it is not yet clear why the stereochemistry of 24 changed depending on the catalyst used, we now believe that the present isomerization of (η4-diene)metal intermediates to 2-pyranone 24 may proceed through addition-elimination of a H-[M] species to a 1,3-diene ligand, generating π-allylmetal intermediates. A π-allylrhodium intermediate has energetically favorable syw-type configuration leading to the selective formation of (E)-24, while a sterically congested anti-type π-allylruthenium species, which is also postulated as a key intermediate in our previously reported ruthenium-catalyzed codimerization of 1,3-dienes with acrylic compounds, could be generated to give (Z)-24 in good selectivity. See: Mitsudo, T, Zhang, S.-W, Kondo, T, Watanabe, Y. Tetrahedron Lett. 1992, 33, 341
    • 4-diene)metal intermediates to 2-pyranone 24 may proceed through addition-elimination of a H-[M] species to a 1,3-diene ligand, generating π-allylmetal intermediates. A π-allylrhodium intermediate has energetically favorable syw-type configuration leading to the selective formation of (E)-24, while a sterically congested anti-type π-allylruthenium species, which is also postulated as a key intermediate in our previously reported ruthenium-catalyzed codimerization of 1,3-dienes with acrylic compounds, could be generated to give (Z)-24 in good selectivity. See: Mitsudo, T.; Zhang, S.-W.; Kondo, T.; Watanabe, Y. Tetrahedron Lett. 1992, 33, 341.
  • 245
    • 0001319774 scopus 로고    scopus 로고
    • A related construction of phenols by the thermolysis of 4-alkenylcyclobutenones, which were prepared by palladium-catalyzed cross-coupling of 4-chlorocyclobutenones with alkenylstannyl and/or zinc reagents, has been reported. Krysan, D. J.; Gurski, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1992, 114, 1412.
    • A related construction of phenols by the thermolysis of 4-alkenylcyclobutenones, which were prepared by palladium-catalyzed cross-coupling of 4-chlorocyclobutenones with alkenylstannyl and/or zinc reagents, has been reported. Krysan, D. J.; Gurski, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1992, 114, 1412.
  • 247
    • 0033972360 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see: Rigby, J. H. Synlett 2000, 1.
    • (2000) Synlett , pp. 1
    • Rigby, J.H.1
  • 259
    • 4544240649 scopus 로고    scopus 로고
    • and references therein. For nickel catalysts, see
    • For nickel catalysts, see: Duang, H. A.; Cross, M. J.; Louie, J. J. Am. Chem. Soc. 2004, 126, 11438; and references therein.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 11438
    • Duang, H.A.1    Cross, M.J.2    Louie, J.3
  • 263
    • 0142196884 scopus 로고    scopus 로고
    • A theoretical study was also reported by Kirchner and co-worker, see: b
    • A theoretical study was also reported by Kirchner and co-worker, see: (b) Schmid, R.; Kirchner, K. J. Org. Chem. 2003, 68, 8339.
    • (2003) J. Org. Chem , vol.68 , pp. 8339
    • Schmid, R.1    Kirchner, K.2
  • 265
    • 34548173261 scopus 로고    scopus 로고
    • and references therein
    • Tanaka, K. Synlett 2007, 1977; and references therein.
    • (2007) Synlett , pp. 1977
    • Tanaka, K.1
  • 267
    • 33644933863 scopus 로고    scopus 로고
    • Most recently, the unusual [2+2+2] cocyclization of alkenylisocyanates and alkynes via CO migration has been reported by Rovis and co-worker, see: Yu, R. T.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2782.
    • Most recently, the unusual [2+2+2] cocyclization of alkenylisocyanates and alkynes via CO migration has been reported by Rovis and co-worker, see: Yu, R. T.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2782.
  • 269
    • 41349090781 scopus 로고    scopus 로고
    • 2
    • 2
  • 277
    • 22944485617 scopus 로고    scopus 로고
    • (e) Ma, S. Chem. Rev. 2005, 105, 2829.
    • (2005) Chem. Rev , vol.105 , pp. 2829
    • Ma, S.1


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