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Volumn 48, Issue 35, 2007, Pages 6109-6112

Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters

Author keywords

Benzyl acetate; Homogeneous catalysis; Nucleophilic substitution; Palladium

Indexed keywords

ACETIC ACID; ACETIC ACID DERIVATIVE; ALCOHOL; AMINE; BENZENE DERIVATIVE; BENZYL ACETATE; ESTER DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; SOLVENT;

EID: 34547466757     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.157     Document Type: Article
Times cited : (34)

References (22)
  • 4
    • 0032568384 scopus 로고    scopus 로고
    • Review:
    • Review:. Guibé F. Tetrahedron 54 (1998) 2967
    • (1998) Tetrahedron , vol.54 , pp. 2967
    • Guibé, F.1
  • 14
    • 1542769690 scopus 로고
    • Chatani and Murai reported the cobalt-catalyzed homologation of benzyl acetate involving the activation of the benzylic carbon-oxygen bond:
    • Chatani and Murai reported the cobalt-catalyzed homologation of benzyl acetate involving the activation of the benzylic carbon-oxygen bond:. Chatani N., Sano T., Ohe K., Kawasaki Y., and Murai S. J. Org. Chem. 55 (1990) 5923
    • (1990) J. Org. Chem. , vol.55 , pp. 5923
    • Chatani, N.1    Sano, T.2    Ohe, K.3    Kawasaki, Y.4    Murai, S.5
  • 16
    • 2442665166 scopus 로고    scopus 로고
    • Shimizu and Yamamoto reported Heck reaction of benzyl trifluoroacetate:
    • Shimizu and Yamamoto reported Heck reaction of benzyl trifluoroacetate:. Narahashi H., Yamamoto A., and Shimizu I. Chem. Lett. 33 (2004) 348
    • (2004) Chem. Lett. , vol.33 , pp. 348
    • Narahashi, H.1    Yamamoto, A.2    Shimizu, I.3
  • 19
    • 34547401663 scopus 로고    scopus 로고
    • note
    • Although the effect of the alcoholic solvent is unclear, we speculate that hydrogen bonding between alcoholic proton and carbonyl oxygen of benzyl acetate may weaken the benzylic carbon-oxygen bond.
  • 20
    • 34547407938 scopus 로고    scopus 로고
    • note
    • 4, and evaporated under reduced pressure. The residue was purified with a flash column chromatography on silica gel (EtOAc/hexane).
  • 21
    • 34547486084 scopus 로고    scopus 로고
    • note
    • As with the reaction of benzylic carbonates (Ref. 4a), the reactivity of benzyl acetate 1a was lower than those of both electron-rich and -poor substrate. We speculated that the electron-donating group of 1 weakened the benzylic C-O bond. Meanwhile, the electron-withdrawing group may favor the pre-coordination of the palladium(0) on the aromatic ring of the benzylic ester.
  • 22
    • 34547485539 scopus 로고    scopus 로고
    • note
    • 3-benzyl ligand on palladium. Triethylamine might be required for neutralizing the acetic acid liberated from benzyl acetate. The reaction conditions were insufficient for the reaction of 1a with malonates, resulting in no formation of 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.