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Volumn 63, Issue 12, 1998, Pages 4034-4038

A Modified Procedure for Sonogashira Couplings: Synthesis and Characterization of a Bisporphyrin, 1,1-Bis[zinc(II) 5′-ethynyl-10′,15′,20′-trimesitylporphyrinyl] niethylenecyclohexane

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EID: 1542603521     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980098o     Document Type: Article
Times cited : (85)

References (31)
  • 10
    • 0001430189 scopus 로고
    • Dolphin, D., Ed.; Academic Press: New York
    • Oxidation of meso-substituted metalloporphyrins yields stable, π-radical cations, see: J. Fajer and M. S. Davis, in: The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 4, pp 197- 256.
    • (1978) The Porphyrins , vol.4 , pp. 197-256
    • Fajer, J.1    Davis, M.S.2
  • 17
    • 1542571066 scopus 로고    scopus 로고
    • note
    • Unlike reactions to produce the bisporphyrin, the yield of monoporphyrin 8 was high. However, 10 equiv of (trimethylsilyl)- acetylene was used. This large excess is not economically feasible for reactions using 9 and is precluded by stoichiometry requirements in reactions using 6.
  • 20
    • 1542466473 scopus 로고    scopus 로고
    • This reaction produced reduced 7 which is difficult to separate from the desired porphyrin
    • This reaction produced reduced 7 which is difficult to separate from the desired porphyrin.
  • 24
    • 85087248417 scopus 로고    scopus 로고
    • note
    • 25,26 excellent yields for double couplings but uses excess alkyne. Because of our different stoichiometry requirements, and our more elaborate coupling partners, we cannot use an excess of alkyne.
  • 27
    • 1542466471 scopus 로고    scopus 로고
    • Procedures in which solvent and reagents were added to the reaction flask in a glovebox also failed to give clean reactions
    • Procedures in which solvent and reagents were added to the reaction flask in a glovebox also failed to give clean reactions.
  • 31
    • 0001556646 scopus 로고    scopus 로고
    • Negishi recently reported Pd-mediated synthesis of terminal alkynes, obviating TMS protection altogether: Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957.
    • (1997) J. Org. Chem. , vol.62 , pp. 8957
    • Negishi, E.1    Kotora, M.2    Xu, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.