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Volumn , Issue 19, 2009, Pages 3219-3227

Sequential hiyaima coupling/narasaka acylation reaction of (e)-1,2-disilylethene: rapid assembly of α,β-unsaturated carbonyl motifs

Author keywords

Acylation; Cross coupling; Ketones; Palladium; Rhodium

Indexed keywords


EID: 67650917426     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900288     Document Type: Article
Times cited : (23)

References (63)
  • 1
    • 33845280492 scopus 로고
    • For representative examples of bismetallated lynchpin-type reagents for polyene synthesis, see: a
    • For representative examples of bismetallated lynchpin-type reagents for polyene synthesis, see: a) A. M. Echavarren, J. K. Stille, J. Am. Chem. Soc 1988, 110, 1557;
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 1557
    • Echavarren, A.M.1    Stille, J.K.2
  • 5
    • 0001360393 scopus 로고    scopus 로고
    • T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 11.018;
    • e) T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 11.018;
  • 10
    • 34247101151 scopus 로고    scopus 로고
    • R. S. Coleman, X. Lu, I. Modelo, J. Am. Chem. Soc 2007, 129, 3826.
    • j) R. S. Coleman, X. Lu, I. Modelo, J. Am. Chem. Soc 2007, 129, 3826.
  • 18
    • 67650913024 scopus 로고    scopus 로고
    • See the Supporting Information for full details
    • See the Supporting Information for full details.
  • 20
    • 67650867012 scopus 로고    scopus 로고
    • Interestingly, the reaction was completed after 2 h and gave a 70:30 mixture of (E)- and (Z)-l,2-bis-silylethene 5.
    • Interestingly, the reaction was completed after 2 h and gave a 70:30 mixture of (E)- and (Z)-l,2-bis-silylethene 5.
  • 21
    • 0012414457 scopus 로고    scopus 로고
    • Note that the formation of 4 was reported as a 29:71 mixture of (E)-4 and the internal adduct formed by ruthenium-catalyzed hydrosilylation; see: Y. Kawanami, Y. Sonoda, T. Mori, K. Yamamoto, Org. Lett. 2002, 4, 2825.
    • Note that the formation of 4 was reported as a 29:71 mixture of (E)-4 and the internal adduct formed by ruthenium-catalyzed hydrosilylation; see: Y. Kawanami, Y. Sonoda, T. Mori, K. Yamamoto, Org. Lett. 2002, 4, 2825.
  • 23
    • 67650860845 scopus 로고    scopus 로고
    • Eds, F. Diederich, P. J. Stang, Wiley-VCH, Weinheim, chapter 10;
    • b) T. Hiyama in Metal-Catalyzed, Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, chapter 10;
    • (1998) Metal-Catalyzed, Cross-Coupling Reactions
    • Hiyama, T.1
  • 34
    • 0000386089 scopus 로고    scopus 로고
    • See the Supporting Information. a K. Kokubo, M. Matsumasa, M. Miura, M. Nomura, J. Org. Chem. 1996, 61, 6941;
    • See the Supporting Information. a) K. Kokubo, M. Matsumasa, M. Miura, M. Nomura, J. Org. Chem. 1996, 61, 6941;
  • 37
    • 67650892969 scopus 로고    scopus 로고
    • Under rhodium catalysis conditions, no coupling reaction occurred with 5 and iodobenzene in the presence of TBAF, whereas only degradation was observed when 1,2-bis-silylethene 5 and acetic anhydride were subjected to palladium acylation catalysis.
    • Under rhodium catalysis conditions, no coupling reaction occurred with 5 and iodobenzene in the presence of TBAF, whereas only degradation was observed when 1,2-bis-silylethene 5 and acetic anhydride were subjected to palladium acylation catalysis.
  • 38
    • 67650860844 scopus 로고    scopus 로고
    • This reagent was prepared by quaternarisation of nBu3N from Merrifield resin followed by anionic exchange with NaF
    • 3N from Merrifield resin followed by anionic exchange with NaF.
  • 44
    • 33947574070 scopus 로고    scopus 로고
    • S. D. Yang, L. Y. Wu, Z. Y. Yan, Z. L. Pan, Y. M. Liang, J. Mol. Catal. A 2007, 268, 1.07.
    • e) S. D. Yang, L. Y. Wu, Z. Y. Yan, Z. L. Pan, Y. M. Liang, J. Mol. Catal. A 2007, 268, 1.07.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.