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Volumn 46, Issue 33, 2005, Pages 5507-5510

One-pot synthesis of α-alkylated nitriles with carbonyl compounds through consecutive aldol reaction/hydrogenation using a hydrotalcite-supported palladium nanoparticle as a multifunctional heterogeneous catalyst

Author keywords

Alkylation of nitrile; Aldol reaction; Heterogeneous catalyst; Hydrogenation; Hydrotalcite; One pot synthesis; Palladium

Indexed keywords

ALKYL GROUP; CARBONYL DERIVATIVE; HYDROGEN; HYDROTALCITE; NANOPARTICLE; NITRILE; PALLADIUM;

EID: 22144481359     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.053     Document Type: Article
Times cited : (53)

References (32)
  • 1
  • 2
    • 0034505430 scopus 로고    scopus 로고
    • For excellent reports of one-pot reactions, see: K.M. Koeller, and C.-H. Wong Chem. Rev. 100 2000 4465
    • (2000) Chem. Rev. , vol.100 , pp. 4465
    • Koeller, K.M.1    Wong, C.-H.2
  • 23
    • 32744457670 scopus 로고    scopus 로고
    • note
    • For example, the reaction of ethyl cyanoacetate (1 ) with benzyl alcohol using the Ru/HT afforded undesirable benzyl cyanoacetate (base-catalyzed transesterification product) and the alkylation product was not formed.
  • 28
    • 32744454558 scopus 로고    scopus 로고
    • note
    • 3, was obtained from TOMITA Pharmaceutical Co., Ltd.
  • 29
    • 32744454811 scopus 로고    scopus 로고
    • note
    • The Pd/carbons were purchased from N.E. Chemcat Co. Ltd (0.5 wt %) and Wako Pure Chemical Ind., Ltd (5.0 wt %).
  • 30
    • 32744467279 scopus 로고    scopus 로고
    • note
    • In a large-scale reaction, 1 (1.70 g, 15 mmol), 2 (1.59 g, 15 mmol), the Pd/HT (0.1 wt %, 0.60 g, Pd: 0.006 mmol), and toluene (20 mL) was used. After the aldol reaction (80°C, 3 h) and the hydrogenation (80°C, 20 h), the catalyst was filtered and GC analysis of the filtrate showed a 97% yield of 4. The filtrate was evaporated and the crude product was purified by distillation (180°C/5.0 mmHg) to afford pure product (2.9 g, 95% yield, TON = 2380).
  • 31
    • 32744464201 scopus 로고    scopus 로고
    • note
    • 2) using 1 with 2, corresponding alkylated product (4 ) was obtained, however, the yield was low (61%, after 1 h, 80°C) compared to that in the consecutive reaction and benzyl alcohol was formed as a byproduct.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.