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Volumn 71, Issue 24, 2006, Pages 9128-9138

Palladium-catalyzed coupling of allenylphosphonates, phenylallenes, and allenyl esters: Remarkable salt effect and routes to novel benzofurans and isocoumarins

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYST ACTIVITY; MOLECULAR STRUCTURE; PHENOLS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

EID: 33751582220     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061525y     Document Type: Article
Times cited : (113)

References (88)
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    • Reviews: Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, section 3.12
    • Reviews: (a) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 4, section 3.12, pp 657-712.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 657-712
    • Donnelly, D.M.X.1    Meegan, M.J.2
  • 41
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    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U.K.
    • (b) Comprehensive Heterocyclic Chemistry II;, Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 2, pp 259-321.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 259-321
  • 66
    • 33751572948 scopus 로고    scopus 로고
    • note
    • 31P NMR: δ 22-23), but it was not isolated. In some cases, there was unreacted allene (∼5%).
  • 67
    • 33751579642 scopus 로고    scopus 로고
    • note
    • 2C=C(Me) [δ(P): 17.0] which could be isolated.
  • 68
    • 33751583696 scopus 로고    scopus 로고
    • note
    • The rest are unidentified products (presumably other isomers) + starting material. By contrast, the allene PhCH=C=CHMe (solvent: N,N-dimethylacetamide) reacts with 3-bromo-5,5-dimethyl-2-cyclohexen-1-one to give a mixture of Z and E isomers; see ref 2a.
  • 69
    • 33751567311 scopus 로고    scopus 로고
    • note
    • For this reason, in reactions using 1b, a lower stoichiometry of aryl iodide (0.8 equiv, cf. Scheme 2) is utilized for optimum yields.
  • 70
    • 33751579489 scopus 로고    scopus 로고
    • note
    • 2 group [δ 2.99, J = 20.8 Hz] is present, but this compound could not be isolated.
  • 72
    • 33751557182 scopus 로고    scopus 로고
    • note
    • One of the reviewers is of the opinion that the differences described here and the absence of such differences for other allenic substrates must be related to better coordinating properties of the P=O moiety, with a possibility of chelated intermediates with a Pd⋯O=P coordination.
  • 81
    • 3543103135 scopus 로고    scopus 로고
    • The allene PhCH=C=CH(Me) gave a mixture of E/Z isomers: Kato, F.; Hiroi, K. Chem. Pharm. Bull. 2004, 52, 95.
    • (2004) Chem. Pharm. Bull. , vol.52 , pp. 95
    • Kato, F.1    Hiroi, K.2
  • 83
    • 33751556854 scopus 로고    scopus 로고
    • note
    • Such a proton is not available in the reaction of 1a with iodobenzene, and hence a simple substitution product is not obtained.
  • 85
    • 0001668016 scopus 로고
    • Wiley & Sons: New York
    • (a) Lang, R. W.; Hansen, H. -J. Organic Synthesis; Wiley & Sons: New York, 1990: Collect. Vol. 7, p 232.
    • (1990) Organic Synthesis , vol.7 COLLECT. VOL. , pp. 232
    • Lang, R.W.1    Hansen, H.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.