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Volumn 16, Issue 2, 2014, Pages 440-443

Diborylation of alkynyl MIDA boronates and sequential chemoselective suzuki-miyaura couplings: A formal carboborylation of alkynes

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EID: 84896788886     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403326z     Document Type: Article
Times cited : (47)

References (66)
  • 2
    • 0032383670 scopus 로고    scopus 로고
    • For reviews on diborylation of unsaturated C-C bonds, see:
    • (a) Marder, T. B.; Norman, N. C. Top. Catal. 1998, 5, 63.
    • (1998) Top. Catal. , vol.5 , pp. 63
    • Marder, T.B.1    Norman, N.C.2
  • 10
    • 0000975959 scopus 로고    scopus 로고
    • Liebeskind, L. S., Eds.; JAI: Stanford
    • (b) Miyaura, N. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Eds.; JAI: Stanford, 1998; Vol. 6, p 187
    • (1998) Advances in Metal-Organic Chemistry , vol.6 , pp. 187
    • Miyaura, N.1
  • 25
    • 0002888768 scopus 로고    scopus 로고
    • In some cases high chemoselectivity was achieved, but the reactions are accompanied by double-coupled products and/or a mixture of regioisomers
    • In some cases high chemoselectivity was achieved, but the reactions are accompanied by double-coupled products and/or a mixture of regioisomers; see: (a) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Lett. 1996, 1117
    • (1996) Chem. Lett. , vol.1117
    • Ishiyama, T.1    Yamamoto, M.2    Miyaura, N.3
  • 34
    • 33846588529 scopus 로고    scopus 로고
    • Nitrogen-based protective groups for the boronyl group:
    • Nitrogen-based protective groups for the boronyl group: (a) Noguchi, H.; Hojo, K.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 758
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 758
    • Noguchi, H.1    Hojo, K.2    Suginome, M.3
  • 49
    • 0029739722 scopus 로고    scopus 로고
    • Although diborylation of alkynylboron compounds are known, no further reactions toward the formed C-B bond have been explored. For example
    • Although diborylation of alkynylboron compounds are known, no further reactions toward the formed C-B bond have been explored. For example, see: (a) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1501
    • Maderna, A.1    Pritzkow, H.2    Siebert, W.3
  • 62
    • 0002888768 scopus 로고    scopus 로고
    • Examples of chemoselective Suzuki-Miyaura coupling reactions of vic-diborylated alkenes
    • Examples of chemoselective Suzuki-Miyaura coupling reactions of vic-diborylated alkenes: (a) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Lett. 1996, 1117
    • (1996) Chem. Lett. , vol.1117
    • Ishiyama, T.1    Yamamoto, M.2    Miyaura, N.3
  • 64
    • 84896775948 scopus 로고    scopus 로고
    • When the reaction was conducted with the more reactive benzyl bromide, the desired 5 was obtained in 2% NMR yield. We thus assume that Kornblum oxidation took place under the reaction conditions because of a detection of benzaldehyde after the reaction
    • When the reaction was conducted with the more reactive benzyl bromide, the desired 5 was obtained in 2% NMR yield. We thus assume that Kornblum oxidation took place under the reaction conditions because of a detection of benzaldehyde after the reaction.


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