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Volumn 22, Issue 17, 2003, Pages 3608-3610

Ruthenium-catalyzed one-pot β-alkylation of secondary alcohols with primary alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; HYDROGENATION; KETONES;

EID: 0041428071     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030307h     Document Type: Article
Times cited : (160)

References (29)
  • 3
    • 0002782655 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K.
    • Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 3, pp 1-63.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 1-63
    • Caine, D.1
  • 16
    • 0035966201 scopus 로고    scopus 로고
    • 3 (5 mol %)/KOH (3 equiv)/dioxane/80 °C/20 h, afforded 1,3-diphenylpropan-1-ol and 1,3-diphenylpropan-1-one in 77% and 3% isolated yields, respectively: Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020.
    • (2001) J. Org. Chem. , vol.66 , pp. 9020
    • Cho, C.S.1    Kim, B.T.2    Kim, T.-J.3    Shim, S.C.4
  • 17
    • 0037190865 scopus 로고    scopus 로고
    • 3 (2 mol %)/KOH (1 equiv)/1-dodecene (1 equiv)/dioxane/80 °C/20 h gave 1,3-diphenylpropan-1-one and 1,3-diphenylpropan-1-ol in 82% and 2% isolated yields, respectively. On the other hand, when the reaction was carried out in the absence of 1-dodecene, 1,3-diphenylpropan-1-one was formed in 70% yield along with a considerable amount of 1,3-diphenylpropan-1-ol (14%); Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Tetrahedron Lett. 2002, 43, 7987.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7987
    • Cho, C.S.1    Kim, B.T.2    Kim, T.-J.3    Shim, S.C.4
  • 23
    • 0042754202 scopus 로고    scopus 로고
    • It is known that initial oxidation proceeds via oxidative addition of the O-H bond to Ru and subsequent β-hydrogen elimination.
    • It is known that initial oxidation proceeds via oxidative addition of the O-H bond to Ru and subsequent β-hydrogen elimination.
  • 24
    • 0042252940 scopus 로고    scopus 로고
    • Bases are used as promoters in transition-metal-catalyzed transfer hydrogenation of ketones to alcohols
    • Bases are used as promoters in transition-metal-catalyzed transfer hydrogenation of ketones to alcohols.
  • 26
    • 0041752372 scopus 로고    scopus 로고
    • note
    • However, treatment of diphenylacetylene under the employed conditions scarcely afforded stilbenes. This result indicates that diphenylacetylene is converted to stilbenes by transfer hydrogenation from the starting alcohols 1a and 2a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.