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Volumn 65, Issue 15, 2000, Pages 4537-4542

Highly selective palladium-catalyzed synthesis of protected α,β-unsaturated methyl ketones and 2-alkoxy-1,3-butadienes. High-speed chemistry by microwave flash heating

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; BROMIDE; ETHER DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

EID: 0034725834     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000070o     Document Type: Article
Times cited : (58)

References (54)
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    • (1994) Advances in Metal-Organic Chemistry , vol.3 , pp. 97-224
    • Larock, R.C.1
  • 9
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    • Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT
    • Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 5, pp 153-260.
    • (1996) Advances in Metal-Organic Chemistry , vol.5 , pp. 153-260
    • Jeffery, T.1
  • 11
    • 0343580756 scopus 로고    scopus 로고
    • U.S. Patent 5248829, 1993
    • DeVries, R. A. U.S. Patent 5248829, 1993.
    • DeVries, R.A.1
  • 24
    • 0343580754 scopus 로고    scopus 로고
    • note
    • To ensure full conversion of the vinyl bromide or vinyl triflate and to suppress homocoupling, 5 equiv of 1a was utilized.
  • 25
    • 0342275549 scopus 로고    scopus 로고
    • Caution! Thallium acetate is a very toxic salt
    • Caution! Thallium acetate is a very toxic salt.
  • 27
    • 0342710711 scopus 로고    scopus 로고
    • note
    • α,β-Unsaturated dioxolanes are very sensitive to hydrolysis, even that occurring on silica gel or on alumina columns. See refs 28-30.
  • 37
    • 0342275548 scopus 로고    scopus 로고
    • note
    • Generally, solvents with tan δ greater than 0.1 are effective in microwave flash heating. See ref 38.
  • 39
    • 0343580753 scopus 로고    scopus 로고
    • note
    • Clearly, in the absence of a correct temperature profile, a reaction may not be reproducible when different microwave heating systems are used.
  • 40
    • 0007100175 scopus 로고    scopus 로고
    • Van Eldik, R., Hubbard, C. D., Eds.; John Wiley & Sons and Spektrum Akademischer Verlag: New York
    • Mingos, D. M. P.; Whittaker, A. G. In Chemistry Under Extreme or Non-Classical Conditions; Van Eldik, R., Hubbard, C. D., Eds.; John Wiley & Sons and Spektrum Akademischer Verlag: New York, 1997; pp 479-514.
    • (1997) Chemistry under Extreme or Non-Classical Conditions , pp. 479-514
    • Mingos, D.M.P.1    Whittaker, A.G.2
  • 42
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    • note
    • Organic solvents superheat under microwave irradiation even at atmospheric pressure; see ref 43.
  • 48
    • 0343580752 scopus 로고    scopus 로고
    • note
    • 3, which was employed in the initial studies.
  • 54
    • 0343580751 scopus 로고    scopus 로고
    • note
    • Acetal formation from α,β-unsaturated ketones using ethylene glycol and strong protic acids typically requires a large amount of acid and often leads to formation of undesirable side products (e.g., β,γ-unsaturated acetals). See refs 1, 2, 28-30, and 55-58.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.