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Volumn 133, Issue 1, 2011, Pages 32-34

Rhodium-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALCOHOL; ALKENYL; ARYLACETYLENES; ENOL ETHERS; HIGH YIELD; HYDROALKOXYLATION; RHODIUM COMPLEXES; RHODIUM-CATALYZED; TERMINAL ACETYLENE;

EID: 78650975736     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1097385     Document Type: Article
Times cited : (83)

References (49)
  • 1
    • 78650970448 scopus 로고
    • Patai, P. Ed.; John Wiley & Sons: Chichester, Chapter 17
    • Fischer, P. In The Chemistry of Functional Groups, Patai, P. Ed.; John Wiley & Sons: Chichester, 1980, Suppl. E., Chapter 17
    • (1980) The Chemistry of Functional Groups , vol.11 , Issue.SUPPL. E. , pp. 4890-4892
    • Fischer, P.1
  • 5
  • 19
    • 0032755406 scopus 로고    scopus 로고
    • Representative reviews
    • Representative reviews: McDonald, F. E. Chem. Eur. J. 1999, 5, 3103-3106
    • (1999) Chem. Eur. J. , vol.5 , pp. 3103-3106
    • McDonald, F.E.1
  • 32
    • 78650975936 scopus 로고    scopus 로고
    • See the Supporting Information for more details.
    • See the Supporting Information for more details.
  • 33
    • 34250117487 scopus 로고
    • In similar reaction conditions, 8-quinolinolato rhodium complexes were reported to catalyze cyclotrimerization of phenylacetylene:, See the Supporting Information for other reactions catalyzed by 8-quinolinolato rhodium compelxes.
    • In similar reaction conditions, 8-quinolinolato rhodium complexes were reported to catalyze cyclotrimerization of phenylacetylene: Shestakova, V. S., Shestakov, G. K., Yureva, L. P., Belyi, A. A., and Temkin, O. N. Russ. Chem. Bull. 1985, 34, 485-487 See the Supporting Information for other reactions catalyzed by 8-quinolinolato rhodium compelxes.
    • (1985) Russ. Chem. Bull. , vol.34 , pp. 485-487
    • Shestakova, V.S.1    Shestakov, G.K.2    Yureva, L.P.3    Belyi, A.A.4    Temkin, O.N.5
  • 34
    • 78650974989 scopus 로고    scopus 로고
    • Some isolated yields are much lower than GC (NMR) yields due to their volatility and/or low stability.
    • Some isolated yields are much lower than GC (NMR) yields due to their volatility and/or low stability.
  • 35
    • 78650991193 scopus 로고    scopus 로고
    • The reaction of 1-octyne with 2a in the presence of 3 gave a small amount (3% NMR yield) of the corresponding anti-Markovnikov addition product.
    • The reaction of 1-octyne with 2a in the presence of 3 gave a small amount (3% NMR yield) of the corresponding anti-Markovnikov addition product.
  • 36
    • 78650996961 scopus 로고    scopus 로고
    • note
    • The reaction of tri(isopropyl)silylacetylene with 2a afforded only a trace amount (< 10% NMR yield) of the addition product under the standard reaction conditions. Other silyl acetylenes, such as trimethylsilyl-, triethylsilyl-, triphenylsilyl-, and tert -butyldimethylsilylacetylene, were not effective as substrates.
  • 37
    • 78650985294 scopus 로고    scopus 로고
    • Allyl and benzyl alcohol did not give the desired enol ether when used as O -nucleophiles. Acetic acid reacted under the standard reaction conditions, and the corresponding anti-Markovnikov addition product, β-styryl acetate, was produced in 28% GC yield (Z / E = 54/46).
    • Allyl and benzyl alcohol did not give the desired enol ether when used as O -nucleophiles. Acetic acid reacted under the standard reaction conditions, and the corresponding anti-Markovnikov addition product, β-styryl acetate, was produced in 28% GC yield (Z / E = 54/46).
  • 38
    • 78650990845 scopus 로고    scopus 로고
    • Mechanistic investigation by deuterium labeling experiments has been difficult due to rapid exchange of protons between MeOH and arylacetylenes.
    • Mechanistic investigation by deuterium labeling experiments has been difficult due to rapid exchange of protons between MeOH and arylacetylenes.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.