메뉴 건너뛰기




Volumn 39, Issue 17, 2000, Pages 3070-3072

A highly active catalyst system for intermolecular hydroacylation

Author keywords

C H activation; Homogeneous catalysis; Hydroacylations; Ketones; Rhodium

Indexed keywords

ALDEHYDE; ALKENE; ANILINE; BENZOIC ACID; KETONE; PICOLINE DERIVATIVE; RHODIUM;

EID: 0034283369     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000901)39:17<3070::AID-ANIE3070>3.0.CO;2-G     Document Type: Article
Times cited : (161)

References (36)
  • 9
    • 0000360319 scopus 로고    scopus 로고
    • and references therein
    • i) B. Bosnich, Acc. Chem. Res. 1998, 31, 667-674, and references therein.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 667-674
    • Bosnich, B.1
  • 19
    • 0031905843 scopus 로고    scopus 로고
    • c) C-H. Jun, C.-W. Huh, S.-J. Na, Angew. Chem. 1998, 110, 150- 152; Angew. Chem. Int. Ed. 1998, 37, 145-147;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 145-147
  • 22
    • 0003678023 scopus 로고
    • American Chemical Society, Washington, DC
    • The oxidation of bezaldehyde occurs spontaneously on contact with air: M. Hudlický, Oxidations in Organic Chemistry, American Chemical Society, Washington, DC, 1990, p. 174.
    • (1990) Oxidations in Organic Chemistry , pp. 174
    • Hudlický, M.1
  • 23
    • 0343449313 scopus 로고    scopus 로고
    • note
    • To confirm the effect of carboxylic acid, the hydroacylation of 1-hexene with freshly purified benzaldehyde was performed with henzoic acid under the reaction conditions depicted in Equation (1). While it took 24 h to obtain a 72% yield without benzoic acid, the reaction time was shortened to 6 h with benzoic acid, and a 75% yield of heptanophenone 6 a was obtained.
  • 27
    • 0343885112 scopus 로고    scopus 로고
    • note
    • The reactivity of 2a with 9 towards hydroiminoacylation was not enhanced by the addition of 7. This implies that carboxylic acid does not affect the hydroiminoacylation step. Therefore, we assume that the rate-determining step is the formation of 9.
  • 28
    • 0343885111 scopus 로고    scopus 로고
    • note
    • It is also possible that Ia condenses with 4 to form 9. However, the condensation of 1a with 8 is more facile than with 4. When an equimolar mixture of 1a, 4, and 8 was heated at 130°C for 10 min 1a was completely consumed and the ratio of 9:11 was determined as 10:90 by GC.
  • 36
    • 0342316832 scopus 로고    scopus 로고
    • note
    • It can be explained by the fact that the protonated aldimine is more electrophilic than the aldehyde. Since the aldimine is more basic than the aldehyde, it is the dominant reactant in the presence of acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.