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Volumn 524, Issue 7565, 2015, Pages 330-334

Switching on elusive organometallic mechanisms with photoredox catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; NICKEL; TRANSITION ELEMENT; ALCOHOL DERIVATIVE; BROMIDE; BROMINATED HYDROCARBON; CARBON; OXYGEN;

EID: 84939839315     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature14875     Document Type: Article
Times cited : (489)

References (30)
  • 1
    • 84900544451 scopus 로고    scopus 로고
    • Recent advances in homogeneous nickel catalysis
    • Tasker, S. Z., Standley, E. A. & Jamison, T. F. Recent advances in homogeneous nickel catalysis. Nature 509, 299-309 (2014).
    • (2014) Nature , vol.509 , pp. 299-309
    • Tasker, S.Z.1    Standley, E.A.2    Jamison, T.F.3
  • 2
    • 12344251733 scopus 로고    scopus 로고
    • Nickel-catalyzed cross-couplings of unactivated alkyl halides and pseudohalides with organometallic compounds
    • Netherton, M. R. & Fu, G. C. Nickel-catalyzed cross-couplings of unactivated alkyl halides and pseudohalides with organometallic compounds. Adv. Synth. Catal. 346, 1525-1532 (2004).
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1525-1532
    • Netherton, M.R.1    Fu, G.C.2
  • 3
    • 78650383080 scopus 로고    scopus 로고
    • Visible light photoredox catalysis: Applications in organic synthesis
    • Narayanam, J. M. R. & Stephenson, C. R. J. Visible light photoredox catalysis: applications in organic synthesis. Chem. Soc. Rev. 40, 102-113 (2011).
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 102-113
    • Narayanam, J.M.R.1    Stephenson, C.R.J.2
  • 4
    • 84880124916 scopus 로고    scopus 로고
    • Visible light photoredox catalysis with transition metal complexes: Applications in organic synthesis
    • Prier, C. K.,Rankic, D. A.&MacMillan,D.W.C. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem. Rev. 113, 5322-5363 (2013).
    • (2013) Chem. Rev. , vol.113 , pp. 5322-5363
    • Prier, C.K.1    Rankic, D.A.2    MacMillan, D.W.C.3
  • 5
    • 84896707663 scopus 로고    scopus 로고
    • Solarsynthesis:prospects invisible light photocatalysis
    • Schultz, D. M.&Yoon, T. P.Solarsynthesis:prospects invisible light photocatalysis. Science 343, 1239176 (2014).
    • (2014) Science , vol.343 , pp. 1239176
    • Schultz, D.M.1    Yoon, T.P.2
  • 6
    • 53349122064 scopus 로고    scopus 로고
    • Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes
    • Nicewicz, D. A. & MacMillan, D. W. C. Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes. Science 322, 77-80 (2008).
    • (2008) Science , vol.322 , pp. 77-80
    • Nicewicz, D.A.1    MacMillan, D.W.C.2
  • 7
    • 67650283342 scopus 로고    scopus 로고
    • Efficient visible light photocatalysis of [212] enone cycloadditions
    • Ischay, M. A., Anzovino, M. E.,Du, J.&Yoon, T. P. Efficient visible light photocatalysis of [212] enone cycloadditions. J. Am. Chem. Soc. 130, 12886-12887 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 12886-12887
    • Ischay, M.A.1    Anzovino, M.E.2    Du, J.3    Yoon, T.P.4
  • 8
    • 67649625293 scopus 로고    scopus 로고
    • Electron-transfer photoredox catalysis: Development of a tin-free reductive dehalogenation reaction
    • Narayanam, J. M. R., Tucker, J. W. & Stephenson, C. R. J. Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction. J. Am. Chem. Soc. 131, 8756-8757 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 8756-8757
    • Narayanam, J.M.R.1    Tucker, J.W.2    Stephenson, C.R.J.3
  • 9
    • 84875546445 scopus 로고    scopus 로고
    • Photoredox activation for the direct b-arylation of ketones and aldehydes
    • Pirnot, M. T., Rankic, D. A., Martin, D. B. C. & MacMillan, D. W. C. Photoredox activation for the direct b-arylation of ketones and aldehydes. Science 339, 1593-1596 (2013).
    • (2013) Science , vol.339 , pp. 1593-1596
    • Pirnot, M.T.1    Rankic, D.A.2    Martin, D.B.C.3    MacMillan, D.W.C.4
  • 10
    • 84897915531 scopus 로고    scopus 로고
    • Dual catalysis sees the light: Combining photoredox with organo-, acid, and transition-metal catalysis
    • Hopkinson, M. N., Sahoo, B., Li, J.-L. & Glorius, F. Dual catalysis sees the light: combining photoredox with organo-, acid, and transition-metal catalysis. Chemistry 20, 3874-3886 (2014).
    • (2014) Chemistry , vol.20 , pp. 3874-3886
    • Hopkinson, M.N.1    Sahoo, B.2    Li, J.-L.3    Glorius, F.4
  • 11
    • 33847031721 scopus 로고    scopus 로고
    • Photo-activation of Pd-catalyzed Sonogashira coupling using a Ru/bipyridine complex as energy transfer agent
    • Osawa, M., Nagai, H. & Akita, M. Photo-activation of Pd-catalyzed Sonogashira coupling using a Ru/bipyridine complex as energy transfer agent. Dalton Trans.827-829 (2007).
    • (2007) Dalton Trans. , pp. 827-829
    • Osawa, M.1    Nagai, H.2    Akita, M.3
  • 12
    • 83055161587 scopus 로고    scopus 로고
    • Room-temperature C-H arylation: Merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis
    • Kalyani, D., McMurtrey, K. B., Neufeldt, S. R. & Sanford, M. S. Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis. J. Am. Chem. Soc. 133, 18566-18569 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 18566-18569
    • Kalyani, D.1    McMurtrey, K.B.2    Neufeldt, S.R.3    Sanford, M.S.4
  • 13
    • 84861863992 scopus 로고    scopus 로고
    • Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I
    • Ye, Y. & Sanford, M. S. Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I. J. Am. Chem. Soc. 134, 9034-9037 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 9034-9037
    • Ye, Y.1    Sanford, M.S.2
  • 14
    • 84876487932 scopus 로고    scopus 로고
    • Combining gold and photoredox catalysis: Visible light-mediated oxy-and aminoarylation of alkenes
    • Sahoo,B.,Hopkinson, M. N.&Glorius, F.Combining gold and photoredox catalysis: visible light-mediated oxy-and aminoarylation of alkenes. J. Am. Chem. Soc. 135, 5505-5508 (2013).
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 5505-5508
    • Sahoo, B.1    Hopkinson, M.N.2    Glorius, F.3
  • 15
    • 84904800842 scopus 로고    scopus 로고
    • Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
    • Tellis, J. C., Primer, D. N. & Molander, G. A. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis. Science 345, 433-436 (2014).
    • (2014) Science , vol.345 , pp. 433-436
    • Tellis, J.C.1    Primer, D.N.2    Molander, G.A.3
  • 16
    • 84904797499 scopus 로고    scopus 로고
    • Merging photoredox with nickel catalysis: Coupling of a-carboxyl sp3-carbons with aryl halides
    • Zuo, Z. et al. Merging photoredox with nickel catalysis: coupling of a-carboxyl sp3-carbons with aryl halides. Science 345, 437-440 (2014).
    • (2014) Science , vol.345 , pp. 437-440
    • Zuo, Z.1
  • 17
    • 84930633780 scopus 로고
    • Oxygen-atom transfer from nitrous oxide to a nickelmetallacycle. Synthesis, structure, andreactions of [cyclic] (2,29-bipyridine)Ni(OCH2CH2CH2CH2)
    • Matsunaga, P. T., Hillhouse, G. L. & Rheingold, A. L. Oxygen-atom transfer from nitrous oxide to a nickelmetallacycle. Synthesis, structure, andreactions of [cyclic] (2,29-bipyridine)Ni(OCH2CH2CH2CH2). J. Am. Chem. Soc. 115, 2075-2077 (1993).
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2075-2077
    • Matsunaga, P.T.1    Hillhouse, G.L.2    Rheingold, A.L.3
  • 18
    • 0000424220 scopus 로고
    • Oxygen-atom transfer from nitrous oxide (N5N5O) to nickel alkyls. Syntheses and reactions of nickel(II) alkoxides
    • Matsunaga, P. T., Mavropoulos, J. C. & Hillhouse, G. L. Oxygen-atom transfer from nitrous oxide (N5N5O) to nickel alkyls. Syntheses and reactions of nickel(II) alkoxides. Polyhedron 14, 175-185 (1995).
    • (1995) Polyhedron , vol.14 , pp. 175-185
    • Matsunaga, P.T.1    Mavropoulos, J.C.2    Hillhouse, G.L.3
  • 19
    • 0030758961 scopus 로고    scopus 로고
    • Carbon-oxygen reductive-elimination from nickel(II) oxametallacycles and factors that control formation of ether, aldehyde, alcohol, or ester products
    • Han, R. & Hillhouse, G. L. Carbon-oxygen reductive-elimination from nickel(II) oxametallacycles and factors that control formation of ether, aldehyde, alcohol, or ester products. J. Am. Chem. Soc. 119, 8135-8136 (1997).
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8135-8136
    • Han, R.1    Hillhouse, G.L.2
  • 20
    • 84924778325 scopus 로고    scopus 로고
    • Design, synthesis, and carbon-heteroatom coupling reactions of organometallic nickel(IV) complexes
    • Camasso, N. M. & Sanford, M. S. Design, synthesis, and carbon-heteroatom coupling reactions of organometallic nickel(IV) complexes. Science 347, 1218-1220 (2013).
    • (2013) Science , vol.347 , pp. 1218-1220
    • Camasso, N.M.1    Sanford, M.S.2
  • 21
    • 84933060297 scopus 로고    scopus 로고
    • Aromatic methoxylation and hydroxylation by organometallic high-valent nickel complexes
    • Zhou, W., Schultz, J. W., Rath, N. P. & Mirica, L. M. Aromatic methoxylation and hydroxylation by organometallic high-valent nickel complexes. J. Am. Chem. Soc. 137, 7604-7607 (2015).
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 7604-7607
    • Zhou, W.1    Schultz, J.W.2    Rath, N.P.3    Mirica, L.M.4
  • 22
    • 1642378847 scopus 로고    scopus 로고
    • Theoretical studies on C-heteroatom bond formation via reductive elimination fromgroup 10 M(PH3)2(CH3)(X) species (X5CH3, NH2, OH, SH) and the determination of metal-X bond strengths using density functional theory
    • Macgregor, S. A., Neave, G. W. & Smith, C. Theoretical studies on C-heteroatom bond formation via reductive elimination fromgroup 10 M(PH3)2(CH3)(X) species (X5CH3, NH2, OH, SH) and the determination of metal-X bond strengths using density functional theory. Faraday Discuss. 124, 111-127 (2003).
    • (2003) Faraday Discuss. , vol.124 , pp. 111-127
    • Macgregor, S.A.1    Neave, G.W.2    Smith, C.3
  • 23
    • 0035980304 scopus 로고    scopus 로고
    • An efficient intermolecular palladium-catalyzed synthesis of aryl ethers
    • Torraca, K. E., Huang, X., Parrish, C. A. & Buchwald, S. L. An efficient intermolecular palladium-catalyzed synthesis of aryl ethers. J. Am. Chem. Soc. 123, 10770-10771 (2001).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10770-10771
    • Torraca, K.E.1    Huang, X.2    Parrish, C.A.3    Buchwald, S.L.4
  • 24
    • 0037149634 scopus 로고    scopus 로고
    • Copper-catalyzed coupling of aryl iodides with aliphatic alcohols
    • Wolter, M., Nordmann,G., Job, G. E.&Buchwald, S. L.Copper-catalyzed coupling of aryl iodides with aliphatic alcohols. Org. Lett. 4, 973-976 (2002).
    • (2002) Org. Lett. , vol.4 , pp. 973-976
    • Wolter, M.1    Nordmann, G.2    Job, G.E.3    Buchwald, S.L.4
  • 25
    • 0037047555 scopus 로고    scopus 로고
    • Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bondforming cross-couplings
    • Kataoka,N., Shelby, Q., Stambuli, J. P. & Hartwig, J. F. Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bondforming cross-couplings. J. Org. Chem. 67, 5553-5566 (2002).
    • (2002) J. Org. Chem. , vol.67 , pp. 5553-5566
    • Kataoka, N.1    Shelby, Q.2    Stambuli, J.P.3    Hartwig, J.F.4
  • 26
    • 0000058170 scopus 로고    scopus 로고
    • Nickel-vs. Palladium-catalyzed synthesis of protected phenols from aryl halides
    • Mann, G. & Hartwig, J. F. Nickel-vs. palladium-catalyzed synthesis of protected phenols from aryl halides. J. Org. Chem. 62, 5413-5418 (1997).
    • (1997) J. Org. Chem. , vol.62 , pp. 5413-5418
    • Mann, G.1    Hartwig, J.F.2
  • 27
    • 0001724313 scopus 로고
    • Rates and mechanismof biphenyl synthesis catalyzed by electrogenerated coordinatively unsaturated nickel complexes
    • Amatore, C.& Jutand, A. Rates and mechanismof biphenyl synthesis catalyzed by electrogenerated coordinatively unsaturated nickel complexes. Organometallics 7, 2203-2214 (1988).
    • (1988) Organometallics , vol.7 , pp. 2203-2214
    • Amatore, C.1    Jutand, A.2
  • 28
    • 28044466429 scopus 로고    scopus 로고
    • Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex
    • Lowry, M. S. et al. Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex. Chem. Mater. 17, 5712-5719 (2005).
    • (2005) Chem. Mater. , vol.17 , pp. 5712-5719
    • Lowry, M.S.1
  • 29
    • 57949109399 scopus 로고    scopus 로고
    • Halide ligands - More than just s-donors? A structural and spectroscopic study of homologous organonickel complexes
    • Klein, A. et al. Halide ligands - more than just s-donors? A structural and spectroscopic study of homologous organonickel complexes. Inorg. Chem. 47, 11324-11333 (2008).
    • (2008) Inorg. Chem. , vol.47 , pp. 11324-11333
    • Klein, A.1
  • 30
    • 2942684055 scopus 로고    scopus 로고
    • Investigation of the reductive coupling of aryl halides and/or ethylchloroacetate electrocatalyzed by the precursor NiX2(bpy) with X-5Cl-, Br-or MeSO3-and bpy52,29-dipyridyl
    • Durandetti, M., Devaud, M. & Perichon, J. Investigation of the reductive coupling of aryl halides and/or ethylchloroacetate electrocatalyzed by the precursor NiX2(bpy) with X-5Cl-, Br-or MeSO3-and bpy52,29-dipyridyl. New J. Chem. 20, 659-667 (1996).
    • (1996) New J. Chem. , vol.20 , pp. 659-667
    • Durandetti, M.1    Devaud, M.2    Perichon, J.3


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