메뉴 건너뛰기




Volumn 48, Issue 5, 2015, Pages 1485-1493

How low does iron go? Chasing the active species in fe-catalyzed cross-coupling reactions

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; IRON DERIVATIVE;

EID: 84929583433     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00042     Document Type: Article
Times cited : (216)

References (51)
  • 1
    • 84903215414 scopus 로고
    • Action des Dèrivés Halogénés sur les Magnésiens Aromatiques en Prèsence de Chlorure Ferrique
    • Vavon, G.; Mottez, P. Action des Dèrivés Halogénés sur les Magnésiens Aromatiques en Prèsence de Chlorure Ferrique C. R. Hebd. Seances Acad. Sci. 1944, 218, 557-559
    • (1944) C. R. Hebd. Seances Acad. Sci. , vol.218 , pp. 557-559
    • Vavon, G.1    Mottez, P.2
  • 3
    • 84929594436 scopus 로고    scopus 로고
    • The Development of Iron Catalysts for Cross-Coupling Reactions
    • Bedford, R. B.; Brenner, P. B. The Development of Iron Catalysts for Cross-Coupling Reactions Top. Organomet. Chem. 2015, 10.1007/3418-2015-99
    • (2015) Top. Organomet. Chem.
    • Bedford, R.B.1    Brenner, P.B.2
  • 4
    • 0037083916 scopus 로고    scopus 로고
    • Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents with Aryl Chlorides, Tosylates, and Triflates
    • Fürstner, A.; Leitner, A. Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents with Aryl Chlorides, Tosylates, and Triflates Angew. Chem., Int. Ed. 2002, 41, 609-612
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 609-612
    • Fürstner, A.1    Leitner, A.2
  • 6
    • 4544294922 scopus 로고    scopus 로고
    • Cross-Coupling of Alkyl Halides with Aryl Grignard Reagents Catalyzed by a Low-Valent Iron Complex
    • Martin, R.; Fürstner, A. Cross-Coupling of Alkyl Halides with Aryl Grignard Reagents Catalyzed by a Low-Valent Iron Complex Angew. Chem., Int. Ed. 2004, 43, 3955-3957
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3955-3957
    • Martin, R.1    Fürstner, A.2
  • 7
    • 0034671743 scopus 로고    scopus 로고
    • Transition Metal Catalyzed Preparation of Grignard Compounds
    • Bogdanović, B.; Schwickardi, M. Transition Metal Catalyzed Preparation of Grignard Compounds Angew. Chem., Int. Ed. 2000, 39, 4610-4612
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4610-4612
    • Bogdanović, B.1    Schwickardi, M.2
  • 8
    • 37049129212 scopus 로고
    • Preparation and Crystal Structure of Cyclopentadienyl-1,2-bis(diphenylphosphino)ethaneironmagnesium Bromide Tris(tetrahydrofuran), a Transition-Metal Grignard Reagent
    • Felkin, H.; Knowles, P. J.; Meunier, B.; Mitschler, A.; Ricard, L.; Weiss, R. Preparation and Crystal Structure of Cyclopentadienyl-1,2-bis(diphenylphosphino)ethaneironmagnesium Bromide Tris(tetrahydrofuran), a Transition-Metal Grignard Reagent J. Chem. Soc., Chem. Commun. 1974, 44
    • (1974) J. Chem. Soc., Chem. Commun. , pp. 44
    • Felkin, H.1    Knowles, P.J.2    Meunier, B.3    Mitschler, A.4    Ricard, L.5    Weiss, R.6
  • 9
    • 84876554344 scopus 로고    scopus 로고
    • Synthesis and Reactions of β-Diketiminate-Supported Complexes with Mg-Fe or Yb-Fe Bonds
    • Blake, M. P.; Kaltsoyannis, N.; Mountford, P. Synthesis and Reactions of β-Diketiminate-Supported Complexes with Mg-Fe or Yb-Fe Bonds Chem. Commun. 2013, 49, 3315-3317
    • (2013) Chem. Commun. , vol.49 , pp. 3315-3317
    • Blake, M.P.1    Kaltsoyannis, N.2    Mountford, P.3
  • 10
    • 46949098763 scopus 로고    scopus 로고
    • Preparation, Structure, and Reactivity of Nonstabilized Organoiron Compounds. Implications for Iron-Catalyzed Cross Coupling Reactions
    • Fürstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard, R.; Lehmann, C. W. Preparation, Structure, and Reactivity of Nonstabilized Organoiron Compounds. Implications for Iron-Catalyzed Cross Coupling Reactions J. Am. Chem. Soc. 2008, 130, 8773-8787
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8773-8787
    • Fürstner, A.1    Martin, R.2    Krause, H.3    Seidel, G.4    Goddard, R.5    Lehmann, C.W.6
  • 11
    • 80053584879 scopus 로고    scopus 로고
    • Catalytic Properties of Low Oxidation State Iron Complexes in Cross-Coupling Reactions: Anthracene Iron(-I) Complexes as Competent Catalysts
    • Weber, K.; Schnöckelborg, E.-M.; Wolf, R. Catalytic Properties of Low Oxidation State Iron Complexes in Cross-Coupling Reactions: Anthracene Iron(-I) Complexes as Competent Catalysts ChemCatChem 2011, 3, 1572-1577
    • (2011) ChemCatChem , vol.3 , pp. 1572-1577
    • Weber, K.1    Schnöckelborg, E.-M.2    Wolf, R.3
  • 12
    • 69049084551 scopus 로고    scopus 로고
    • Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents: A New Catalyst Combination of N-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides
    • Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents: A New Catalyst Combination of N-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides J. Am. Chem. Soc. 2009, 131, 11949-11963
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 11949-11963
    • Hatakeyama, T.1    Hashimoto, S.2    Ishizuka, K.3    Nakamura, M.4
  • 13
    • 84903975993 scopus 로고    scopus 로고
    • Selective Kumada Biaryl Cross-Coupling Reaction Enabled by an Iron(III) Alkoxide-N-Heterocyclic Carbene Catalyst System
    • Chua, Y.-Y.; Duong, H. Selective Kumada Biaryl Cross-Coupling Reaction Enabled by an Iron(III) Alkoxide-N-Heterocyclic Carbene Catalyst System Chem. Commun. 2014, 50, 8424-8427
    • (2014) Chem. Commun. , vol.50 , pp. 8424-8427
    • Chua, Y.-Y.1    Duong, H.2
  • 14
    • 84876540773 scopus 로고    scopus 로고
    • Fe-Catalyzed Kumada-Type Alkyl-Alkyl Cross-Coupling. Evidence for the Intermediacy of Fe(I) Complexes
    • Guisan-Ceinos, M.; Tato, F.; Bunuel, E.; Calle, P.; Cardenas, D. J. Fe-Catalyzed Kumada-Type Alkyl-Alkyl Cross-Coupling. Evidence for the Intermediacy of Fe(I) Complexes Chem. Sci. 2013, 4, 1098-1104
    • (2013) Chem. Sci. , vol.4 , pp. 1098-1104
    • Guisan-Ceinos, M.1    Tato, F.2    Bunuel, E.3    Calle, P.4    Cardenas, D.J.5
  • 15
    • 1642361256 scopus 로고    scopus 로고
    • Iron-Catalyzed Cross-Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents
    • Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. Iron-Catalyzed Cross-Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents J. Am. Chem. Soc. 2004, 126, 3686-3687
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 3686-3687
    • Nakamura, M.1    Matsuo, K.2    Ito, S.3    Nakamura, E.4
  • 16
    • 25144465934 scopus 로고    scopus 로고
    • Simple Iron-Amine Catalysts for the Cross-Coupling of Aryl Grignards with Alkyl Halides Bearing β-Hydrogens
    • Bedford, R. B.; Bruce, D. W.; Frost, R. M.; Hird, M. Simple Iron-Amine Catalysts for the Cross-Coupling of Aryl Grignards with Alkyl Halides Bearing β-Hydrogens Chem. Commun. 2005, 4161-4163
    • (2005) Chem. Commun. , pp. 4161-4163
    • Bedford, R.B.1    Bruce, D.W.2    Frost, R.M.3    Hird, M.4
  • 17
  • 18
    • 69949165772 scopus 로고    scopus 로고
    • Effect of TMEDA on Iron-Catalyzed Coupling Reactions of ArMgX with Alkyl Halides
    • Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. Effect of TMEDA on Iron-Catalyzed Coupling Reactions of ArMgX with Alkyl Halides J. Am. Chem. Soc. 2009, 131, 6078-6079
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 6078-6079
    • Noda, D.1    Sunada, Y.2    Hatakeyama, T.3    Nakamura, M.4    Nagashima, H.5
  • 21
    • 84873973860 scopus 로고    scopus 로고
    • Ligand-Controlled Iron-Catalyzed Cross Coupling of Benzylic Chlorides with Aryl Grignard Reagents
    • Kawamura, S.; Nakamura, M. Ligand-Controlled Iron-Catalyzed Cross Coupling of Benzylic Chlorides with Aryl Grignard Reagents Chem. Lett. 2013, 42, 183-185
    • (2013) Chem. Lett. , vol.42 , pp. 183-185
    • Kawamura, S.1    Nakamura, M.2
  • 22
    • 84898906567 scopus 로고    scopus 로고
    • A Practical Procedure for Iron-Catalyzed Cross-Coupling Reactions of Sterically Hindered Aryl-Grignard Reagents with Primary Alkyl Halides
    • Sun, C.-L.; Krause, H.; Fürstner, A. A Practical Procedure for Iron-Catalyzed Cross-Coupling Reactions of Sterically Hindered Aryl-Grignard Reagents with Primary Alkyl Halides Adv. Synth. Catal. 2014, 356, 1281-1291
    • (2014) Adv. Synth. Catal. , vol.356 , pp. 1281-1291
    • Sun, C.-L.1    Krause, H.2    Fürstner, A.3
  • 24
    • 84903286971 scopus 로고    scopus 로고
    • A Combined Mössbauer, Magnetic Circular Dichroism, and Density Functional Theory Approach for Iron Cross-Coupling Catalysis: Electronic Structure, in Situ Formation, and Reactivity of Iron-Mesityl-Bisphosphines
    • Daifuku, S. L.; Al-Afyouni, M. H.; Snyder, B. E. R.; Kneebone, J. L.; Neidig, M. L. A Combined Mössbauer, Magnetic Circular Dichroism, and Density Functional Theory Approach for Iron Cross-Coupling Catalysis: Electronic Structure, in Situ Formation, and Reactivity of Iron-Mesityl-Bisphosphines J. Am. Chem. Soc. 2014, 136, 9132-9143
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 9132-9143
    • Daifuku, S.L.1    Al-Afyouni, M.H.2    Snyder, B.E.R.3    Kneebone, J.L.4    Neidig, M.L.5
  • 25
    • 33645025382 scopus 로고    scopus 로고
    • Iron Nanoparticles in the Coupling of Alkyl Halides with Aryl Grignard Reagents
    • Bedford, R. B.; Betham, M.; Bruce, D. W.; Davis, S. A.; Frost, R. M.; Hird, M. Iron Nanoparticles in the Coupling of Alkyl Halides with Aryl Grignard Reagents Chem. Commun. 2006, 1398-1400
    • (2006) Chem. Commun. , pp. 1398-1400
    • Bedford, R.B.1    Betham, M.2    Bruce, D.W.3    Davis, S.A.4    Frost, R.M.5    Hird, M.6
  • 27
    • 84908611558 scopus 로고    scopus 로고
    • Isolation and Characterization of a Tetramethyliron(III) Ferrate: An Intermediate in the Reduction Pathway of Ferric Salts with MeMgBr
    • Al-Afyouni, M. H.; Fillman, K. L.; Brennessel, W. W.; Neidig, M. L. Isolation and Characterization of a Tetramethyliron(III) Ferrate: An Intermediate in the Reduction Pathway of Ferric Salts with MeMgBr J. Am. Chem. Soc. 2014, 136, 15457-15460
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 15457-15460
    • Al-Afyouni, M.H.1    Fillman, K.L.2    Brennessel, W.W.3    Neidig, M.L.4
  • 29
    • 0347266352 scopus 로고    scopus 로고
    • Crystal Structure of "[Li(Et2O)]4[FePh4]": Corrigendum and Reformulation. A Remarkable Example of a False Solution in a Wrong Space Group
    • Jefferis, J. M.; Girolami, G. S. Crystal Structure of "[Li(Et2O)]4[FePh4]": Corrigendum and Reformulation. A Remarkable Example of a False Solution in a Wrong Space Group Organometallics 1998, 17, 3630-3632
    • (1998) Organometallics , vol.17 , pp. 3630-3632
    • Jefferis, J.M.1    Girolami, G.S.2
  • 31
    • 33847802043 scopus 로고
    • Synthesis of Olefins. Cross Coupling of Alkenyl Halides and Grignard Reagents Catalyzed by Iron Complexes
    • Neumann, S. M.; Kochi, J. K. Synthesis of Olefins. Cross Coupling of Alkenyl Halides and Grignard Reagents Catalyzed by Iron Complexes J. Org. Chem. 1975, 40, 599-606
    • (1975) J. Org. Chem. , vol.40 , pp. 599-606
    • Neumann, S.M.1    Kochi, J.K.2
  • 32
    • 0001109080 scopus 로고
    • Mechanistic Studies of Iron Catalysis in the Cross Coupling of Alkenyl Halides and Grignard Reagents
    • Smith, R. S.; Kochi, J. K. Mechanistic Studies of Iron Catalysis in the Cross Coupling of Alkenyl Halides and Grignard Reagents J. Org. Chem. 1976, 41, 502-509
    • (1976) J. Org. Chem. , vol.41 , pp. 502-509
    • Smith, R.S.1    Kochi, J.K.2
  • 33
    • 84887055182 scopus 로고    scopus 로고
    • On the Oxidation State of Iron in Iron-Mediated C-C Couplings
    • Hedström, A.; Lindstedt, E.; Norrby, P.-O. On the Oxidation State of Iron in Iron-Mediated C-C Couplings J. Organomet. Chem. 2013, 748, 51-55
    • (2013) J. Organomet. Chem. , vol.748 , pp. 51-55
    • Hedström, A.1    Lindstedt, E.2    Norrby, P.-O.3
  • 34
    • 84857335789 scopus 로고    scopus 로고
    • Low Temperature Studies of Iron-Catalyzed Cross-Coupling of Alkyl Grignard Reagents with Aryl Electrophiles
    • Kleimark, J.; Larsson, P.-F.; Emamy, P.; Hedström, A.; Norrby, P.-O. Low Temperature Studies of Iron-Catalyzed Cross-Coupling of Alkyl Grignard Reagents with Aryl Electrophiles Adv. Synth. Catal. 2012, 354, 448-456
    • (2012) Adv. Synth. Catal. , vol.354 , pp. 448-456
    • Kleimark, J.1    Larsson, P.-F.2    Emamy, P.3    Hedström, A.4    Norrby, P.-O.5
  • 35
    • 80054038099 scopus 로고    scopus 로고
    • Iron-Catalyzed Coupling of Aryl Grignard Reagents with Alkyl Halides: A Competitive Hammett Study
    • Hedström, A.; Bollmann, U.; Bravidor, J.; Norrby, P.-O. Iron-Catalyzed Coupling of Aryl Grignard Reagents with Alkyl Halides: A Competitive Hammett Study Chem. - Eur. J. 2011, 17, 11991-11993
    • (2011) Chem. - Eur. J. , vol.17 , pp. 11991-11993
    • Hedström, A.1    Bollmann, U.2    Bravidor, J.3    Norrby, P.-O.4
  • 37
    • 84961974222 scopus 로고    scopus 로고
    • Activation of Aryl and Heteroaryl Halides by an Iron(I) Complex Generated in the Reduction of [Fe(acac)3] by PhMgBr: Electron Transfer versus Oxidative Addition
    • Lefèvre, G.; Jutand, A. Activation of Aryl and Heteroaryl Halides by an Iron(I) Complex Generated in the Reduction of [Fe(acac)3] by PhMgBr: Electron Transfer versus Oxidative Addition Chem. - Eur. J. 2014, 20, 4796-4805
    • (2014) Chem. - Eur. J. , vol.20 , pp. 4796-4805
    • Lefèvre, G.1    Jutand, A.2
  • 38
    • 84929594438 scopus 로고    scopus 로고
    • Bedford, R. B. Unpublished data (see the Supporting Information for details)
    • Bedford, R. B. Unpublished data (see the Supporting Information for details).
  • 39
    • 32144461712 scopus 로고    scopus 로고
    • Iron-Phosphine, -Phosphite, -Arsine, and -Carbene Catalysts for the Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents
    • Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulos, A. A.; Frost, R. M.; Hird, M. Iron-Phosphine, -Phosphite, -Arsine, and -Carbene Catalysts for the Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents J. Org. Chem. 2006, 71, 1104-1110
    • (2006) J. Org. Chem. , vol.71 , pp. 1104-1110
    • Bedford, R.B.1    Betham, M.2    Bruce, D.W.3    Danopoulos, A.A.4    Frost, R.M.5    Hird, M.6
  • 40
    • 58649099580 scopus 로고    scopus 로고
    • Iron-Catalysed Negishi Coupling of Benzyl Halides and Phosphates
    • Bedford, R. B.; Huwe, M.; Wilkinson, M. C. Iron-Catalysed Negishi Coupling of Benzyl Halides and Phosphates Chem. Commun. 2009, 600-602
    • (2009) Chem. Commun. , pp. 600-602
    • Bedford, R.B.1    Huwe, M.2    Wilkinson, M.C.3
  • 41
    • 60849126986 scopus 로고    scopus 로고
    • Iron-Catalysed Fluoroaromatic Coupling Reactions under Catalytic Modulation with 1,2-Bis(diphenylphosphino)benzene
    • Hatakeyama, T.; Kondo, Y.; Fujiwara, Y.; Takaya, H.; Ito, S.; Nakamura, E.; Nakamura, M. Iron-Catalysed Fluoroaromatic Coupling Reactions under Catalytic Modulation with 1,2-Bis(diphenylphosphino)benzene Chem. Commun. 2009, 1216-1218
    • (2009) Chem. Commun. , pp. 1216-1218
    • Hatakeyama, T.1    Kondo, Y.2    Fujiwara, Y.3    Takaya, H.4    Ito, S.5    Nakamura, E.6    Nakamura, M.7
  • 43
    • 77955361203 scopus 로고    scopus 로고
    • The First Iron-Catalysed Aluminium-Variant Negishi Coupling: Critical Effect of Co-existing Salts on the Dynamic Equilibrium of Arylaluminium Species and Their Reactivity
    • Kawamura, S.; Ishizuka, K.; Takaya, H.; Nakamura, M. The First Iron-Catalysed Aluminium-Variant Negishi Coupling: Critical Effect of Co-existing Salts on the Dynamic Equilibrium of Arylaluminium Species and Their Reactivity Chem. Commun. 2010, 46, 6054-6056
    • (2010) Chem. Commun. , vol.46 , pp. 6054-6056
    • Kawamura, S.1    Ishizuka, K.2    Takaya, H.3    Nakamura, M.4
  • 45
    • 70350330301 scopus 로고    scopus 로고
    • Simple Mixed Fe-Zn Catalysts for the Suzuki Couplings of Tetraarylborates with Benzyl Halides and 2-Halopyridines
    • Bedford, R. B.; Hall, M. A.; Hodges, G. R.; Huwe, M.; Wilkinson, M. C. Simple Mixed Fe-Zn Catalysts for the Suzuki Couplings of Tetraarylborates with Benzyl Halides and 2-Halopyridines Chem. Commun. 2009, 6430-6432
    • (2009) Chem. Commun. , pp. 6430-6432
    • Bedford, R.B.1    Hall, M.A.2    Hodges, G.R.3    Huwe, M.4    Wilkinson, M.C.5
  • 48
    • 84856093673 scopus 로고    scopus 로고
    • Stereospecific Cross-Coupling between Alkenylboronates and Alkyl Halides Catalyzed by Iron-Bisphosphine Complexes
    • Hashimoto, T.; Hatakeyama, T.; Nakamura, M. Stereospecific Cross-Coupling between Alkenylboronates and Alkyl Halides Catalyzed by Iron-Bisphosphine Complexes J. Org. Chem. 2012, 77, 1168-1173
    • (2012) J. Org. Chem. , vol.77 , pp. 1168-1173
    • Hashimoto, T.1    Hatakeyama, T.2    Nakamura, M.3
  • 49
    • 84930619129 scopus 로고    scopus 로고
    • Towards Iron-Catalysed Suzuki Biaryl Cross-Coupling: Unusual Reactivity of 2-Halobenzyl Halides
    • Bedford, R. B.; Gallagher, T.; Pye, D. R.; Savage, W. Towards Iron-Catalysed Suzuki Biaryl Cross-Coupling: Unusual Reactivity of 2-Halobenzyl Halides Synthesis 2015, 10.1055/s-0034-1380135
    • (2015) Synthesis
    • Bedford, R.B.1    Gallagher, T.2    Pye, D.R.3    Savage, W.4
  • 50
    • 84910003839 scopus 로고    scopus 로고
    • Iron-Catalyzed Borylation of Alkyl, Allyl, and Aryl Halides: Isolation of an Iron(I) Boryl Complex
    • Bedford, R. B.; Brenner, P. B.; Carter, E.; Gallagher, T.; Murphy, D. M.; Pye, D. R. Iron-Catalyzed Borylation of Alkyl, Allyl, and Aryl Halides: Isolation of an Iron(I) Boryl Complex Organometallics 2014, 33, 5940-5943
    • (2014) Organometallics , vol.33 , pp. 5940-5943
    • Bedford, R.B.1    Brenner, P.B.2    Carter, E.3    Gallagher, T.4    Murphy, D.M.5    Pye, D.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.