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Volumn 47, Issue 9, 2006, Pages 1375-1379

Pt-Catalyzed sp3 C-H bond activation of o-alkyl substituted aromatic carboxylic acid derivatives for the formation of aryl lactones

Author keywords

Aromatic carboxylates; C H Bond activation; Chelation assistance; Lactones; Shilov catalyst system

Indexed keywords

5,7 DIMETHYLPHTHALIDE; AMIDE; AROMATIC CARBOXYLIC ACID; ARYL LACTONE; BENZOIC ACID DERIVATIVE; ISOTOPE; LACTONE DERIVATIVE; MESITYLENECARBOXYLIC ACID; PALLADIUM; PHTHALIMIDE DERIVATIVE; PLATINUM; UNCLASSIFIED DRUG;

EID: 31444434226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.104     Document Type: Article
Times cited : (110)

References (34)
  • 13
    • 0037028575 scopus 로고    scopus 로고
    • Recent reports from this laboratory regarding on the chelation-assisted approaches: S. Ko, Y. Na, and S. Chang J. Am. Chem. Soc. 124 2002 750 751
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 750-751
    • Ko, S.1    Na, Y.2    Chang, S.3
  • 18
    • 31444453397 scopus 로고    scopus 로고
    • note
    • 2 (5.4 mg, 0.024 mmol). The reaction mixture was stirred for 9 h at 100°C and the product was isolated by a silica gel chromatography (hexane) to give 5,7-dimethylphthalide (2 ) in 44% yield.
  • 19
    • 0037174448 scopus 로고    scopus 로고
    • Recently, Pd-catalyzed decarboxylative Heck olefination of arene carboxylates was reported: A.G. Myers, D. Tanaka, and M.R. Mannion J. Am. Chem. Soc. 124 2002 11250 11251
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11250-11251
    • Myers, A.G.1    Tanaka, D.2    Mannion, M.R.3
  • 23
    • 31444453019 scopus 로고    scopus 로고
    • note
    • 2 (41 mg, 0.18 mmol) in water (0.6 mL, 0.01 M) was heated to 150°C for 18-24 h. After the reaction was over, the reaction mixture was extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was evaporated under the reduced pressure. The crude product was chromatographed on silica gel (hexane) to afford 5,7-dimethylphthalide (2 ) in 56% yield.
  • 24
    • 31444432717 scopus 로고    scopus 로고
    • note
    • Interestingly, when o-tolylacetic acid was employed as a substrate, we only obtained phthalide in 13% yield instead of either 3-isochromanone or 4-methyl-3H-benzofuran-2-one.
  • 25
    • 31444445466 scopus 로고    scopus 로고
    • note
    • In the absence of catalyst, benzamide, benzoate and benzonitrile are completely hydrolyzed to benzoic acid in water at 150°C within 1 h.
  • 26
    • 31444441559 scopus 로고    scopus 로고
    • note
    • D = 1.91 ± 0.04 (average of three time experiments).
  • 32
    • 21844445702 scopus 로고
    • For related mechanistic studies on the C-H bond activation by platinum complexes, see: C.B. Lebrilla, and W.F. Maier J. Am. Chem. Soc. 108 1986 1606 1616
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1606-1616
    • Lebrilla, C.B.1    Maier, W.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.