메뉴 건너뛰기




Volumn 515, Issue 7525, 2014, Pages 100-103

Asymmetric photoredox transition-metal catalysis activated by visible light

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL BROMIDE; IMIDAZOLE DERIVATIVE; IRIDIUM COMPLEX; LEWIS ACID;

EID: 84922773549     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature13892     Document Type: Letter
Times cited : (498)

References (30)
  • 2
    • 72449185228 scopus 로고    scopus 로고
    • Photoredox catalysis with visible light
    • Zeitler, K. Photoredox catalysis with visible light. Angew. Chem. Int. Edn 48, 9785-9789 (2009).
    • (2009) Angew. Chem. Int. Edn , vol.48 , pp. 9785-9789
    • Zeitler, K.1
  • 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
    • Solar synthesis: Prospects in visible light photocatalysis
    • Schultz, D. M.&Yoon, T. P. Solar synthesis: prospects in visible light photocatalysis. Science 343, 1239176 (2014).
    • (2014) Science , vol.343 , pp. 1239176
    • Schultz, D.M.1    Yoon, T.P.2
  • 6
    • 0031573815 scopus 로고    scopus 로고
    • Understanding reactivity patterns of radical cations
    • Schmittel, M. & Burghart, A. Understanding reactivity patterns of radical cations. Angew. Chem. Int. Edn Engl. 36, 2550-2589 (1997).
    • (1997) Angew. Chem. Int. Edn Engl. , vol.36 , pp. 2550-2589
    • Schmittel, M.1    Burghart, A.2
  • 8
    • 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. Chem. Eur. J. 20, 3874-3886 (2014).
    • (2014) Chem. Eur. J. , vol.20 , pp. 3874-3886
    • Hopkinson, M.N.1    Sahoo, B.2    Li, J.-L.3    Glorius, F.4
  • 9
    • 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
  • 10
    • 77957304088 scopus 로고    scopus 로고
    • Enantioselective α-benzylation of aldehydes via photoredox organocatalysis
    • Shih, H.-W., Vander Wal, M. N., Grange, R. L. & MacMillan, D. W. C. Enantioselective α-benzylation of aldehydes via photoredox organocatalysis. J. Am. Chem. Soc. 132, 13600-13603 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 13600-13603
    • Shih, H.-W.1    Vander Wal, M.N.2    Grange, R.L.3    MacMillan, D.W.C.4
  • 11
    • 78751510344 scopus 로고    scopus 로고
    • Metal-free, cooperative asymmetric organophotoredox catalysis with visible light
    • Neumann, M., Füldner, S., König, B. & Zeitler, K. Metal-free, cooperative asymmetric organophotoredox catalysis with visible light. Angew. Chem. Int. Edn 50, 951-954 (2011).
    • (2011) Angew. Chem. Int. Edn , vol.50 , pp. 951-954
    • Neumann, M.1    Füldner, S.2    König, B.3    Zeitler, K.4
  • 12
    • 84859937539 scopus 로고    scopus 로고
    • Visible-light-promoted stereoselective alkylation by combining heterogeneous photocatalysis with organocatalysis
    • Cherevatskaya, M. et al. Visible-light-promoted stereoselective alkylation by combining heterogeneous photocatalysis with organocatalysis. Angew. Chem. Int. Edn 51, 4062-4066 (2012).
    • (2012) Angew. Chem. Int. Edn , vol.51 , pp. 4062-4066
    • Cherevatskaya, M.1
  • 13
    • 68249144236 scopus 로고    scopus 로고
    • Enantioselective α-trifluoromethylation of aldehydes via photoredox organocatalysis
    • Nagib, D. A., Scott, M. E. & MacMillan, D. W. C. Enantioselective α-trifluoromethylation of aldehydes via photoredox organocatalysis. J. Am. Chem. Soc. 131, 10875-10877 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 10875-10877
    • Nagib, D.A.1    Scott, M.E.2    MacMillan, D.W.C.3
  • 14
    • 84862093013 scopus 로고    scopus 로고
    • Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis
    • DiRocco, D. A. & Rovis, T. Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis. J. Am. Chem. Soc. 134, 8094-8097 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 8094-8097
    • DiRocco, D.A.1    Rovis, T.2
  • 15
    • 84880013743 scopus 로고    scopus 로고
    • Catalytic ketyl-olefin cyclizations enabled by proton-coupled electron transfer
    • Tarantino, K. T., Liu, P. & Knowles, R. R. Catalytic ketyl-olefin cyclizations enabled by proton-coupled electron transfer. J. Am. Chem. Soc. 135, 10022-10025 (2013).
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 10022-10025
    • Tarantino, K.T.1    Liu, P.2    Knowles, R.R.3
  • 16
    • 84899543979 scopus 로고    scopus 로고
    • A dual-catalysis approach to enantioselective [2 + 2] photocycloadditions using visible light
    • Du, J., Skubi, K. L., Schultz, D. M. & Yoon, T. P. A dual-catalysis approach to enantioselective [2 + 2] photocycloadditions using visible light. Science 344, 392-396 (2014).
    • (2014) Science , vol.344 , pp. 392-396
    • Du, J.1    Skubi, K.L.2    Schultz, D.M.3    Yoon, T.P.4
  • 17
    • 84888632145 scopus 로고    scopus 로고
    • Photoredox activation and anion binding catalysis in the dual catalytic enantioselective synthesis of b-amino esters
    • Bergonzini, G., Schindler, C. S., Wallentin, C.-J., Jacobsen, E. N. & Stephenson, C. R. J. Photoredox activation and anion binding catalysis in the dual catalytic enantioselective synthesis of b-amino esters. Chem. Sci. 5, 112-116 (2013).
    • (2013) Chem. Sci. , vol.5 , pp. 112-116
    • Bergonzini, G.1    Schindler, C.S.2    Wallentin, C.-J.3    Jacobsen, E.N.4    Stephenson, C.R.J.5
  • 18
    • 24144502430 scopus 로고    scopus 로고
    • Catalytic enantioselective reactions driven by photoinduced electron transfer
    • Bauer, A., Westkämper, F., Grimme, S. & Bach, T. Catalytic enantioselective reactions driven by photoinduced electron transfer. Nature 436, 1139-1140 (2005).
    • (2005) Nature , vol.436 , pp. 1139-1140
    • Bauer, A.1    Westkämper, F.2    Grimme, S.3    Bach, T.4
  • 19
    • 70349895886 scopus 로고    scopus 로고
    • Light-driven enantioselective organocatalysis
    • Müller, C., Bauer, A. & Bach, T. Light-driven enantioselective organocatalysis. Angew. Chem. Int. Edn 48, 6640-6642 (2009).
    • (2009) Angew. Chem. Int. Edn , vol.48 , pp. 6640-6642
    • Müller, C.1    Bauer, A.2    Bach, T.3
  • 20
    • 84887758589 scopus 로고    scopus 로고
    • Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions
    • Brimioulle, R. & Bach, T. Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions. Science 342, 840-843 (2013).
    • (2013) Science , vol.342 , pp. 840-843
    • Brimioulle, R.1    Bach, T.2
  • 21
    • 84899024092 scopus 로고    scopus 로고
    • A chiral thioxanthone as an organocatalyst for enantioselective [2+2] photocycloaddition reactions induced by visible light
    • Alonso, R. & Bach, T. A chiral thioxanthone as an organocatalyst for enantioselective [2+2] photocycloaddition reactions induced by visible light. Angew. Chem. Int. Edn 53, 4368-4371 (2014).
    • (2014) Angew. Chem. Int. Edn , vol.53 , pp. 4368-4371
    • Alonso, R.1    Bach, T.2
  • 22
    • 84883189645 scopus 로고    scopus 로고
    • Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes
    • Arceo, E., Jurberg, I. D., Álvarez-Fernández, A. & Melchiorre, P. Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes. Nature Chem. 5, 750-756 (2013).
    • (2013) Nature Chem. , vol.5 , pp. 750-756
    • Arceo, E.1    Jurberg, I.D.2    Álvarez-Fernández, A.3    Melchiorre, P.4
  • 23
    • 84896847608 scopus 로고    scopus 로고
    • Asymmetric catalysis with substitutionally labile yet stereochemically stable chiral-at-metal iridium(III) complex
    • Huo, H., Fu, C., Harms, K. & Meggers, E. Asymmetric catalysis with substitutionally labile yet stereochemically stable chiral-at-metal iridium(III) complex. J. Am. Chem. Soc. 136, 2990-2993 (2014).
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 2990-2993
    • Huo, H.1    Fu, C.2    Harms, K.3    Meggers, E.4
  • 24
    • 34447320811 scopus 로고    scopus 로고
    • Chiral-at-metal complexes as asymmetric catalysts
    • Fontecave, M., Hamelin, O. & Ménage, S. Chiral-at-metal complexes as asymmetric catalysts. Top. Organomet. Chem. 15, 271-288 (2005).
    • (2005) Top. Organomet. Chem. , vol.15 , pp. 271-288
    • Fontecave, M.1    Hamelin, O.2    Ménage, S.3
  • 25
    • 84859149162 scopus 로고    scopus 로고
    • Chiral-at-metal complexes and their catalytic applications in organic synthesis
    • Bauer, E. B. Chiral-at-metal complexes and their catalytic applications in organic synthesis. Chem. Soc. Rev. 41, 3153-3167 (2012).
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 3153-3167
    • Bauer, E.B.1
  • 26
    • 0038298158 scopus 로고    scopus 로고
    • Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates
    • Evans, D. A., Downey, C. W. & Hubbs, J. L. Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates. J. Am. Chem. Soc. 125, 8706-8707 (2003).
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8706-8707
    • Evans, D.A.1    Downey, C.W.2    Hubbs, J.L.3
  • 27
    • 34547683171 scopus 로고    scopus 로고
    • Application of the DL isomerism of octahedral metal complexes as a chiral source in photochemistry
    • Sato, H. & Yamagishi, A. Application of the DL isomerism of octahedral metal complexes as a chiral source in photochemistry. J. Photochem. Photobiol. C 8, 67-84 (2007).
    • (2007) J. Photoche M. Photobiol. C , vol.8 , pp. 67-84
    • Sato, H.1    Yamagishi, A.2
  • 28
    • 84860327258 scopus 로고    scopus 로고
    • A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates
    • Herrmann, A. T., Smith, L. L. & Zakarian, A. A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates. J. Am. Chem. Soc. 134, 6976-6979 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 6976-6979
    • Herrmann, A.T.1    Smith, L.L.2    Zakarian, A.3
  • 29
    • 84906534625 scopus 로고    scopus 로고
    • The electron is a catalyst
    • Studer, A. & Curran, D. P. The electron is a catalyst. Nature Chem. 6, 765-773 (2014).
    • (2014) Nature Chem. , vol.6 , pp. 765-773
    • Studer, A.1    Curran, D.P.2
  • 30
    • 1542411152 scopus 로고
    • Electron transfer and bond breaking. Examples of passage from a sequential to a concerted mechanism in the electrochemical reductive cleavage of arylmethyl halides
    • Andrieux, C. P., LeGorande, A. & Savéant, J. M. Electron transfer and bond breaking. Examples of passage from a sequential to a concerted mechanism in the electrochemical reductive cleavage of arylmethyl halides. J. Am. Chem. Soc. 114, 6892-6904 (1992).
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6892-6904
    • Andrieux, C.P.1    LeGorande, A.2    Savéant, J.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.