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Volumn 54, Issue 51, 2015, Pages 15545-15549

External-Photocatalyst-Free Visible-Light-Mediated Synthesis of Indolizines

Author keywords

heterocyclic compounds; indolizines; photocatalysis; radicals; visible light

Indexed keywords

LIGHT SOURCES; ORGANIC COMPOUNDS; PHOTOCATALYSIS; SYNTHESIS (CHEMICAL);

EID: 84955170432     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201506868     Document Type: Article
Times cited : (65)

References (53)
  • 4
    • 84955204239 scopus 로고    scopus 로고
    • Selected recent reviews on visible light photoredox catalysis
    • Selected recent reviews on visible light photoredox catalysis:
  • 6
    • 84903279105 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 9969;
    • (2009) Angew. Chem. , vol.121 , pp. 9969
  • 11
    • 84903317897 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 6934;
    • (2012) Angew. Chem. , vol.124 , pp. 6934
  • 15
    • 84880378120 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 4832;
    • (2013) Angew. Chem. , vol.125 , pp. 4832
  • 25
    • 84955208826 scopus 로고    scopus 로고
    • Selected reviews
    • Selected reviews:
  • 31
    • 84955196436 scopus 로고    scopus 로고
    • Review
    • Review:
  • 34
    • 84938422663 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 4841;
    • (2007) Angew. Chem. , vol.119 , pp. 4841
  • 40
    • 84955207460 scopus 로고    scopus 로고
    • See the Supporting Information for more details.
    • See the Supporting Information for more details.
  • 41
    • 84883189645 scopus 로고    scopus 로고
    • Absorption spectra were also recorded of combinations of the reaction components at higher concentrations to investigate any potential excited donor-acceptor (EDA) complexes. No such effect was observed in any of the cases (see the Supporting Information for more details). For an example of EDA complexes, see.
    • Absorption spectra were also recorded of combinations of the reaction components at higher concentrations to investigate any potential excited donor-acceptor (EDA) complexes. No such effect was observed in any of the cases (see the Supporting Information for more details). For an example of EDA complexes, see, E. Arceo, I. D. Jurberg, A. Álvarez-Fernández, P. Melchiorre, Nat. Chem. 2013, 5, 750.
    • (2013) Nat. Chem. , vol.5 , pp. 750
    • Arceo, E.1    Jurberg, I.D.2    Álvarez-Fernández, A.3    Melchiorre, P.4
  • 42
    • 84955205441 scopus 로고    scopus 로고
    • Selected examples
    • Selected examples:
  • 46
    • 84969421433 scopus 로고    scopus 로고
    • + / 3 aa)=-1.9 V versus Ag/AgCl, thus implying that 3 aa∗ is highly reducing (see the Supporting Information)
    • + / 3 aa)=-1.9 V versus Ag/AgCl, thus implying that 3 aa∗ is highly reducing (see the Supporting Information).
  • 47
    • 84888621241 scopus 로고    scopus 로고
    • As the purest class of such reactions, autocatalytic processes have found many roles across the chemical sciences; for a review on autocatalysis, see
    • As the purest class of such reactions, autocatalytic processes have found many roles across the chemical sciences; for a review on autocatalysis, see, A. J. Bissette, S. P. Fletcher, Angew. Chem. Int. Ed. 2013, 52, 12800;
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 12800
    • Bissette, A.J.1    Fletcher, S.P.2
  • 48
    • 84969434343 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 13034.
    • (2013) Angew. Chem. , vol.125 , pp. 13034
  • 49
    • 84969421950 scopus 로고    scopus 로고
    • Indolizine 3 aa is not thought to be acting as a genuine autocatalyst in any of the cases. The increase in the initial rate observed upon adding additional 3 aa would be expected to be greater if this compound was a true autocatalyst. Also, the cyclic voltammetry data of 3 aa indicates that the oxidized form generated upon SET to 1 a is not stable and would lead to decomposition (see the Supporting Information for more details)
    • Indolizine 3 aa is not thought to be acting as a genuine autocatalyst in any of the cases. The increase in the initial rate observed upon adding additional 3 aa would be expected to be greater if this compound was a true autocatalyst. Also, the cyclic voltammetry data of 3 aa indicates that the oxidized form generated upon SET to 1 a is not stable and would lead to decomposition (see the Supporting Information for more details).
  • 50
    • 84969412953 scopus 로고    scopus 로고
    • max=465 nm) as the irradiation source fitted with a long-pass filter at 455 nm, however, resulted in only a 15 % yield of 3 aa (GC yield, cf. 55 % GC yield in the absence of the filter). Indolizine 3 aa was formed in 48 % GC yield using the same light source with a long-pass filter at 400 nm. These results would seem to imply that the visible-light tail of the blue LEDs at wavelengths below 455 nm (and above 400 nm) is mostly responsible for the observed reactivity
    • max=465 nm) as the irradiation source fitted with a long-pass filter at 455 nm, however, resulted in only a 15 % yield of 3 aa (GC yield, cf. 55 % GC yield in the absence of the filter). Indolizine 3 aa was formed in 48 % GC yield using the same light source with a long-pass filter at 400 nm. These results would seem to imply that the visible-light tail of the blue LEDs at wavelengths below 455 nm (and above 400 nm) is mostly responsible for the observed reactivity.
  • 51
    • 84955190335 scopus 로고    scopus 로고
    • The involvement of EDA complexes formed between the indolizine products and the other reaction components was also ruled out by a series of absorption studies (see the Supporting Information for more details)
    • The involvement of EDA complexes formed between the indolizine products and the other reaction components was also ruled out by a series of absorption studies (see the Supporting Information for more details).
  • 52
    • 84969424804 scopus 로고    scopus 로고
    • The involvement of radical chains in this process is supported by the success of the reaction using the thermal radical initiator dibenzoyl peroxide. Conducting the reaction between 1 a and 2 a in the presence of this species (0.5 equiv) at 105 C without light resulted in the formation of 3 aa in 26 % yield (see the Supporting Information for more details)
    • The involvement of radical chains in this process is supported by the success of the reaction using the thermal radical initiator dibenzoyl peroxide. Conducting the reaction between 1 a and 2 a in the presence of this species (0.5 equiv) at 105 C without light resulted in the formation of 3 aa in 26 % yield (see the Supporting Information for more details).


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