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Volumn 133, Issue 22, 2011, Pages 8518-8521

Experimental evidence for cobalt(III)-carbene radicals: Key intermediates in cobalt(II)-based metalloradical cyclopropanation

Author keywords

[No Author keywords available]

Indexed keywords

1 ,5-HEXADIENE; ALLYLIC RADICALS; C-O BOND FORMATION; CARBENES; COBALT COMPLEXES; CYCLOPROPANATION; DFT CALCULATION; DIMERIC STRUCTURE; DINUCLEAR; EXPERIMENTAL EVIDENCE; HYDROGEN ATOMS; METALLOPORPHYRINS; PORPHYRIN COMPLEXES; TOLUENE SOLVENT; UNDERLYING MECHANISM; X RAY STRUCTURAL ANALYSIS;

EID: 79958017831     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja203434c     Document Type: Article
Times cited : (202)

References (44)
  • 18
    • 8844247934 scopus 로고    scopus 로고
    • 2-symmetric chiral porphyrins can be readily prepared through a modular, three-step synthetic scheme
    • 2-symmetric chiral porphyrins can be readily prepared through a modular, three-step synthetic scheme: Chen, Y.; Fields, K. B.; Zhang, X. P. J. Am. Chem. Soc. 2004, 126, 14718
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 14718
    • Chen, Y.1    Fields, K.B.2    Zhang, X.P.3
  • 26
    • 79952607169 scopus 로고    scopus 로고
    • 2-Por*)]-catalyzed enantioselective cyclopropenation of alkynes, see
    • 2-Por*)]-catalyzed enantioselective cyclopropenation of alkynes, see: Cui, X.; Xu, X.; Lu, H.; Zhu, S.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 3304
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 3304
    • Cui, X.1    Xu, X.2    Lu, H.3    Zhu, S.4    Wojtas, L.5    Zhang, X.P.6
  • 27
    • 33947092924 scopus 로고
    • For Co(II)-catalyzed asymmetric cyclopropanation using non-porphyrin-based ligands, see
    • For Co(II)-catalyzed asymmetric cyclopropanation using non-porphyrin-based ligands, see: Nakamura, A.; Konishi, A.; Tatsuno, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3443
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3443
    • Nakamura, A.1    Konishi, A.2    Tatsuno, Y.3    Otsuka, S.4
  • 40
    • 0037176284 scopus 로고    scopus 로고
    • On the basis of IR and DFT investigations, Co(salen) carbene complexes were proposed to have radical character
    • On the basis of IR and DFT investigations, Co(salen) carbene complexes were proposed to have radical character: Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 15152
    • Ikeno, T.1    Iwakura, I.2    Yamada, T.3
  • 43
    • 79957995981 scopus 로고    scopus 로고
    • When preformed 4 (via Scheme 3) was reacted with TEMPO (10 equiv) in toluene at 80 °C for 3 h, no formation of 7 was observed.
    • When preformed 4 (via Scheme 3) was reacted with TEMPO (10 equiv) in toluene at 80 °C for 3 h, no formation of 7 was observed.
  • 44
    • 79958006736 scopus 로고    scopus 로고
    • When ethyl styryldiazoacetate (4 equiv) was reacted with TEMPO (10 equiv) first in toluene for 3 h at 80 °C, followed by addition of [Co(TPP)], no formation of 7 or 4 was observed, even after further reaction for an additional 3 h at 80 °C.
    • When ethyl styryldiazoacetate (4 equiv) was reacted with TEMPO (10 equiv) first in toluene for 3 h at 80 °C, followed by addition of [Co(TPP)], no formation of 7 or 4 was observed, even after further reaction for an additional 3 h at 80 °C.


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