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Volumn 44, Issue 7, 2011, Pages 479-490

Photochemistry of group 6 fischer carbene complexes: Beyond the photocarbonylation reaction

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CHROMIUM; COORDINATION COMPOUND; DRUG DERIVATIVE; ETHYLENE DERIVATIVE; IMINE; KETENE; KETONE; LACTAM; METHANE;

EID: 79960486397     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar100159h     Document Type: Article
Times cited : (67)

References (48)
  • 1
    • 0346265937 scopus 로고
    • Selected reviews on the chemistry of Fischer carbenes. For recent reviews on Fischer carbene complexes, Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York
    • Selected reviews on the chemistry of Fischer carbenes. For recent reviews on Fischer carbene complexes, see: Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Wulff, W.D.1
  • 2
    • 0342471010 scopus 로고    scopus 로고
    • The use of Fischer carbene complexes for the preparation of five- membered carbocyclic rings
    • DOI 10.1016/S0040-4020(99)00981-3, PII S0040402099009813
    • Herndon, J. W. The Use of Fischer Carbene Complexes for the Preparation of Five-Membered Carbocyclic Rings Tetrahedron 2000, 56, 1257-1280 (Pubitemid 30141462)
    • (2000) Tetrahedron , vol.56 , Issue.10 , pp. 1257-1280
    • Herndon, J.W.1
  • 3
    • 0343932676 scopus 로고    scopus 로고
    • Metalloxy Fischer carbene complexes: An efficient strategy to modulate their reactivity
    • PII S0040402000002374
    • Barluenga, J.; Fañanás, F. J. Metalloxy Fischer Carbene Complexes: An Efficient Strategy to Modulate Their Reactivity Tetrahedron 2000, 56, 4597-4628 (Pubitemid 30432049)
    • (2000) Tetrahedron , vol.56 , Issue.27 , pp. 4597-4628
    • Barluenga, J.1    Fananas, F.J.2
  • 4
    • 0034301372 scopus 로고    scopus 로고
    • Di- and Polymetallic Heteroatom Stabilized (Fischer) Metal Carbene Complexes
    • Sierra, M. A. Di- and Polymetallic Heteroatom Stabilized (Fischer) Metal Carbene Complexes Chem. Rev. 2000, 100, 3591-3638
    • (2000) Chem. Rev. , vol.100 , pp. 3591-3638
    • Sierra, M.A.1
  • 5
    • 0034680584 scopus 로고    scopus 로고
    • Fischer Carbene Complexes as Chemical Multitalents: The Incredible Range of Products from Carbenepentacarbonylmetal α,β-Unsaturated Complexes
    • de Meijere, A.; Schirmer, H.; Duestch, M. Fischer Carbene Complexes as Chemical Multitalents: The Incredible Range of Products from Carbenepentacarbonylmetal α,β-Unsaturated Complexes Angew. Chem., Int. Ed. 2000, 39, 3964-4002
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3964-4002
    • De Meijere, A.1    Schirmer, H.2    Duestch, M.3
  • 6
    • 2942609170 scopus 로고    scopus 로고
    • Synthesis of Heterocycles via Group VI Fischer Carbene Complexes
    • Barluenga, J.; Santamaría, J.; Tomás, M. Synthesis of Heterocycles via Group VI Fischer Carbene Complexes Chem. Rev. 2004, 104, 2259-2284
    • (2004) Chem. Rev. , vol.104 , pp. 2259-2284
    • Barluenga, J.1    Santamaría, J.2    Tomás, M.3
  • 7
    • 33846452918 scopus 로고    scopus 로고
    • Fischer carbene complexes: Beautiful playgrounds to study Single Electron Transfer (SET) reactions
    • DOI 10.1002/chem.200601470
    • Sierra, M. A.; Gómez-Gallego, M.; Martínez-Álvarez, R. Fischer Carbene Complexes: Beautiful Playgrounds To Study Single Electron Transfer (SET) Reactions Chem.-Eur. J. 2007, 13, 736-744 (Pubitemid 46144550)
    • (2007) Chemistry - A European Journal , vol.13 , Issue.3 , pp. 736-744
    • Sierra, M.A.1    Gomez-Gallego, M.2    Martinez-Alvarez, R.3
  • 8
    • 54749094326 scopus 로고    scopus 로고
    • Computational and Experimental Tools in Solving some Mechanistic Problems in the Chemistry of Fischer Carbene Complexes
    • Sierra, M. A.; Fernández, I.; Cossío, F. P. Computational and Experimental Tools in Solving some Mechanistic Problems in the Chemistry of Fischer Carbene Complexes Chem. Commun. 2008, 4671-4682
    • (2008) Chem. Commun. , pp. 4671-4682
    • Sierra M., .A.1    Fernández, I.2    Cossío F., .P.3
  • 9
    • 68949157444 scopus 로고    scopus 로고
    • Fischer Carbene Complexes in Organic Synthesis: Metal-Assisted and Metal-Templated Reactions
    • Dötz, K. H.; Stendel, J., Jr. Fischer Carbene Complexes in Organic Synthesis: Metal-Assisted and Metal-Templated Reactions Chem. Rev. 2009, 109, 3227-3274
    • (2009) Chem. Rev. , vol.109 , pp. 3227-3274
    • Dötz K., .H.1    Stendel, J.2
  • 11
    • 0000951659 scopus 로고
    • Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford
    • Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 549
    • Hegedus, L.S.1
  • 12
    • 0001313865 scopus 로고
    • Synthesis of Amino Acids and Peptides Using Chromium Carbene Complex Photochemistry
    • Hegedus, L. S. Synthesis of Amino Acids and Peptides Using Chromium Carbene Complex Photochemistry Acc. Chem. Res. 1995, 28, 299-305
    • (1995) Acc. Chem. Res. , vol.28 , pp. 299-305
    • Hegedus, L.S.1
  • 13
    • 0031585112 scopus 로고    scopus 로고
    • Chromium carbene complex photochemistry in organic synthesis
    • DOI 10.1016/S0040-4020(96)01186-6, PII S0040402096011866
    • Hegedus, L. Chromium Carbene Complexes Photochemistry in Organic Synthesis. S Tetrahedron 1997, 53, 4105-4128 (Pubitemid 27130092)
    • (1997) Tetrahedron , vol.53 , Issue.12 , pp. 4105-4128
    • Hegedus, L.S.1
  • 14
    • 42549140767 scopus 로고    scopus 로고
    • Photochemical reactions as key steps in organic synthesis
    • DOI 10.1021/cr0680336
    • Hoffmann, N. Photochemical Reactions as Key Steps in Organic Synthesis Chem. Rev. 2008, 108, 1052-1103 (Pubitemid 351577856)
    • (2008) Chemical Reviews , vol.108 , Issue.3 , pp. 1052-1103
    • Hoffmann, N.1
  • 17
    • 33845278327 scopus 로고
    • Evidence for the Intermediacy of Chromium-Ketene Complexes in the Synthesis of β-Lactams by the Photolytic Reaction of Chromium-Carbene Complexes with Imines. Use in Amino Acid Synthesis
    • Hegedus, L. S.; de Weck, G.; DAndrea, S. Evidence for the Intermediacy of Chromium-Ketene Complexes in the Synthesis of β-Lactams by the Photolytic Reaction of Chromium-Carbene Complexes with Imines. Use in Amino Acid Synthesis J. Am. Chem. Soc. 1988, 110, 2122-2126
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2122-2126
    • Hegedus, L.S.1    De Weck, G.2    Dandrea, S.3
  • 18
    • 33847798298 scopus 로고
    • MO Calculations on Metal Carbene Complexes and Metal Acyl Complexes. the Importance of the LUMO in Determining the Site of Nucleophilic attack
    • Block, T. J.; Fenske, R. F.; Casey, C. P. MO Calculations on Metal Carbene Complexes and Metal Acyl Complexes. The Importance of the LUMO in Determining the Site of Nucleophilic attack J. Am. Chem. Soc. 1976, 98, 441-443
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 441-443
    • Block, T.J.1    Fenske, R.F.2    Casey, C.P.3
  • 20
  • 21
    • 46949084440 scopus 로고    scopus 로고
    • Electronic Structure of Alkoxychromium(0) Carbene Complexes: A Joint TD-DFT/Experimental Study
    • Lage, M. L.; Fernández, I.; Mancheño, M. J.; Sierra, M. A. Electronic Structure of Alkoxychromium(0) Carbene Complexes: A Joint TD-DFT/Experimental Study Inorg. Chem. 2008, 47, 5253-5258
    • (2008) Inorg. Chem. , vol.47 , pp. 5253-5258
    • Lage, M.L.1    Fernández, I.2    Mancheño, M.J.3    Sierra, M.A.4
  • 22
    • 0034703756 scopus 로고    scopus 로고
    • A Theoretical-Experimental Approach to the Mechanism of the Photocarbonylation of Chromium(0) (Fischer)-Carbene Complexes and Their Reaction with Imines
    • Arrieta, A.; Cossío, F. P.; Fernández, I.; Gómez-Gallego, M.; Lecea, B.; Mancheño, M. J.; Sierra, M. A. A Theoretical-Experimental Approach to the Mechanism of the Photocarbonylation of Chromium(0) (Fischer)-Carbene Complexes and Their Reaction with Imines J. Am. Chem. Soc. 2000, 122, 11509-11510
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11509-11510
    • Arrieta, A.1    Cossío, F.P.2    Fernández, I.3    Gómez-Gallego, M.4    Lecea, B.5    Mancheño, M.J.6    Sierra, M.A.7
  • 23
    • 26844506718 scopus 로고    scopus 로고
    • Computational and experimental studies on the mechanism of the photochemical carbonylation of Group 6 Fischer carbene complexes
    • DOI 10.1002/chem.200400944
    • Fernández, I.; Sierra, M. A.; Gómez-Gallego, M.; Mancheño, M. J.; Cossío, F. P. Computational and Experimental Studies on the Mechanism of the Photochemical Carbonylation of Group 6 Fischer Carbene Complexes Chem.-Eur. J. 2005, 11, 5988-5996 (Pubitemid 41454698)
    • (2005) Chemistry - A European Journal , vol.11 , Issue.20 , pp. 5988-5996
    • Fernandez, I.1    Sierra, M.A.2    Gomez-Gallego, M.3    Mancheno, J.M.4    Cossio, F.P.5
  • 24
    • 0001191690 scopus 로고
    • Photochemistry of Metal Carbonyls
    • This is a general phenomenon in Group 6 metal carbonyl complexes. See ref 3c and Wrighton, M. Photochemistry of Metal Carbonyls Chem. Rev. 1974, 74, 401-430
    • (1974) Chem. Rev. , vol.74 , pp. 401-430
    • Wrighton, M.1
  • 25
    • 18044370097 scopus 로고    scopus 로고
    • A DFT study on hetero-Diels-Alder reactions catalyzed by cobalt complexes: Lewis acidity enhancement as a consequence of spin transition caused by Lewis base coordination
    • DOI 10.1002/anie.200460836
    • For a recent example on Lewis-base-induced triplet-singlet crossing in organometallic compounds, see: Iwakura, I.; Ikeno, T.; Yamada, T. A DFT Study on Hetero-Diels-Alder Reactions Catalyzed by Cobalt Complexes: Lewis Acidity Enhancement as a Consequence of Spin Transition Caused by Lewis Base Coordination Angew. Chem., Int. Ed. 2005, 44, 2524-2527 (Pubitemid 40600320)
    • (2005) Angewandte Chemie - International Edition , vol.44 , Issue.17 , pp. 2524-2527
    • Iwakura, I.1    Ikeno, T.2    Yamada, T.3
  • 26
    • 0037267025 scopus 로고    scopus 로고
    • Spin Forbidden Chemical Reactions of Transition Metal Compounds. New Ideas and New Computational Challenges
    • Poli, R.; Harvey, J. N. Spin Forbidden Chemical Reactions of Transition Metal Compounds. New Ideas and New Computational Challenges Chem. Soc. Rev. 2003, 32, 1-8
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 1-8
    • Poli, R.1    Harvey J., .N.2
  • 27
    • 51649103509 scopus 로고    scopus 로고
    • The Mechanism of the Ketene-Imine (Staudinger) Reaction in Its Centennial: Still an Unsolved Problem?
    • For a recent review, see: Cossío, F. P.; Arrieta, A.; Sierra, M. A. The Mechanism of the Ketene-Imine (Staudinger) Reaction in Its Centennial: Still an Unsolved Problem? Acc. Chem. Res. 2008, 41, 925-936
    • (2008) Acc. Chem. Res. , vol.41 , pp. 925-936
    • Cossío, F.P.1    Arrieta, A.2    Sierra, M.A.3
  • 28
    • 54249153780 scopus 로고    scopus 로고
    • Deeper Insight into the Mechanism of the Reaction of Photogenerated Metallaketenes and Imines
    • Fernández, I.; Sierra, M. A.; Mancheño, M. J.; Gómez-Gallego, M.; Cossío, F. P. Deeper Insight into the Mechanism of the Reaction of Photogenerated Metallaketenes and Imines J. Am. Chem. Soc. 2008, 130, 13892-13899
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 13892-13899
    • Fernández, I.1    Sierra, M.A.2    Mancheño, M.J.3    Gómez-Gallego, M.4    Cossío, F.P.5
  • 29
    • 13644264785 scopus 로고    scopus 로고
    • Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: Mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of β-lactams
    • DOI 10.1021/ja044179f
    • Recent examples: France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. Bifunctional Lewis Acid-Nucleophile-Based Asymmetric Catalysis: Mechanistic Evidence for Imine Activation Working in Tandem with Chiral Enolate Formation in the Synthesis of β-Lactams J. Am. Chem. Soc. 2005, 127, 1206-1215 (Pubitemid 40228691)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.4 , pp. 1206-1215
    • France, S.1    Shah, M.H.2    Weatherwax, A.3    Wack, H.4    Roth, J.P.5    Lectka, T.6
  • 30
    • 24044436551 scopus 로고    scopus 로고
    • Catalytic asymmetric staudinger reactions to form β-lactams: An unanticipated dependence of diastereoselectivity on the choice of the nitrogen substituent
    • DOI 10.1021/ja052058p
    • Lee, E. C.; Hodous, B. L.; Bergin, E.; Shih, C.; Fu, G. C. Catalytic Asymmetric Staudinger Reactions to Form β-Lactams: An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent J. Am. Chem. Soc. 2005, 127, 11586-11587 (Pubitemid 41213338)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.33 , pp. 11586-11587
    • Lee, E.C.1    Hodous, B.L.2    Bergin, E.3    Shih, C.4    Fu, G.C.5
  • 31
    • 4143125756 scopus 로고    scopus 로고
    • Advances in the Catalytic, Asymmetric Synthesis of β-Lactams
    • France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Advances in the Catalytic, Asymmetric Synthesis of β-Lactams Acc. Chem. Res. 2004, 37, 592-600
    • (2004) Acc. Chem. Res. , vol.37 , pp. 592-600
    • France, S.1    Weatherwax, A.2    Taggi, A.E.3    Lectka, T.4
  • 32
    • 0027520117 scopus 로고
    • Regioselectivity of Photochemical Annulations of Chromium Carbene Complexes
    • Examples: Merlic, C. A.; Roberts, W. M. Regioselectivity of Photochemical Annulations of Chromium Carbene Complexes Tetrahedron Lett. 1993, 34, 7397-7382
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7397-7382
    • Merlic, C.A.1    Roberts, W.M.2
  • 33
    • 0000489364 scopus 로고
    • Cyclization Reactions of Chromium Dienylcarbene Complexes. Entry to Ortho-Substituted Aromatic Alcohols via a Designed Photoreaction
    • Merlic, C. A.; Xu, D. Q. Cyclization Reactions of Chromium Dienylcarbene Complexes. Entry to Ortho-Substituted Aromatic Alcohols via a Designed Photoreaction J. Am. Chem. Soc. 1991, 113, 7418-7420
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7418-7420
    • Merlic, C.A.1    Xu, D.Q.2
  • 34
    • 33751385031 scopus 로고
    • Aminobenzannulation via Photocyclization reaction of Chromiumdienyl(amino)carbene complexes. Synthesis of o -Amino Aromatic Alcohols
    • Merlic, C. A.; Xu, D.; Gladstone, B. G. Aminobenzannulation via Photocyclization reaction of Chromiumdienyl(amino)carbene complexes. Synthesis of o -Amino Aromatic Alcohols J. Org. Chem. 1993, 58, 538-545
    • (1993) J. Org. Chem. , vol.58 , pp. 538-545
    • Merlic, C.A.1    Xu, D.2    Gladstone, B.G.3
  • 36
    • 84981903846 scopus 로고
    • Dyotropic Rearrangements, a New Class of Orbital-Symmetry Controlled Reactions. Type i
    • Reetz, M. T. Dyotropic Rearrangements, a New Class of Orbital-Symmetry Controlled Reactions. Type I Angew. Chem., Int. Ed. Engl. 1972, 11, 129-130
    • (1972) Angew. Chem., Int. Ed. Engl. , vol.11 , pp. 129-130
    • Reetz, M.T.1
  • 37
    • 0001455738 scopus 로고
    • Primary and secondary orbital effects in dyotropic rearrangements
    • Dyotropic Reactions: Mechanisms and Synthetic Applications Chem. Rev. 2009, 109, 6687-6711
    • Reetz, M. T. Primary and secondary orbital effects in dyotropic rearrangements Tetrahedron 1973, 29, 2189-2194
    • (1973) Tetrahedron , vol.29 , pp. 2189-2194
    • Reetz, M.T.1
  • 38
    • 75849128042 scopus 로고    scopus 로고
    • Dyotropic Reactions: Mechanisms and Synthetic Applications
    • Fernández, I.; Cossío, F. P.; Sierra, M. A. Dyotropic Reactions: Mechanisms and Synthetic Applications Chem. Rev. 2009, 109, 6687-6711
    • (2009) Chem. Rev. , vol.109 , pp. 6687-6711
    • Fernández, I.1    Cossío F., .P.2    Sierra M., .A.3
  • 41
    • 0002452161 scopus 로고
    • Photochemistry of carboxylic acid derivatives
    • Coyle, J. D. Photochemistry of carboxylic acid derivatives Chem. Rev. 1978, 78, 97-123
    • (1978) Chem. Rev. , vol.78 , pp. 97-123
    • Coyle, J.D.1
  • 43
    • 0000350403 scopus 로고
    • Theoretical Organometallic Chemistry
    • This fragmentation in the position α to the carbene nitrogen atom is predictable on the basis of the isolobal analogy. See: Hoffmann, R. Theoretical Organometallic Chemistry Science 1981, 211, 995-1002
    • (1981) Science , vol.211 , pp. 995-1002
    • Hoffmann, R.1
  • 44
    • 84985520810 scopus 로고
    • Building Bridges between Inorganic and Organic Chemistry
    • Hoffmann, R. Building Bridges Between Inorganic and Organic Chemistry Angew. Chem., Int. Ed. Engl. 1982, 21, 711-724
    • (1982) Angew. Chem., Int. Ed. Engl. , vol.21 , pp. 711-724
    • Hoffmann, R.1
  • 46
  • 47
    • 77953154570 scopus 로고    scopus 로고
    • The Electronic Structure and Photochemistry of Group 6 Bimetallic (Fischer) Carbene Complexes: Beyond the Photocarbonylation Reaction
    • Lage, M. L.; Fernández, I.; Mancheño, M. J.; Gómez-Gallego, M.; Sierra, M. A. The Electronic Structure and Photochemistry of Group 6 Bimetallic (Fischer) Carbene Complexes: Beyond the Photocarbonylation Reaction Chem.-Eur. J. 2010, 16, 6616-6624
    • (2010) Chem.-Eur. J. , vol.16 , pp. 6616-6624
    • Lage, M.L.1    Fernández, I.2    Mancheño, M.J.3    Gómez-Gallego, M.4    Sierra, M.A.5
  • 48
    • 0035969302 scopus 로고    scopus 로고
    • Decomplexation of cyclopentadienylmanganese tricarbonyls under very mild conditions: A novel route to substituted cyclopentadienes and their application in organometallic synthesis
    • DOI 10.1021/om010274a
    • Top, S.; Kaloun, E. B.; Toppi, S.; Herrbach, A.; McGlinchey, M. J.; Jaouen, G. Decomplexation of Cyclopentadienylmanganese Tricarbonyls under Very Mild Conditions: A Novel Route to Substituted Cyclopentadienes and Their Application in Organometallic Synthesis Organometallics 2001, 20, 4554-4561 (Pubitemid 35349253)
    • (2001) Organometallics , vol.20 , Issue.22 , pp. 4554-4561
    • Top, S.1    Kaloun, E.B.2    Toppi, S.3    Herrbach, A.4    McGlinchey, M.J.5    Jaouen, G.6


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