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Volumn 130, Issue 9, 2008, Pages 2754-2755

Palladium-catalyzed carbonylation of aryl tosylates and mesylates

Author keywords

[No Author keywords available]

Indexed keywords

MESYLIC ACID DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

EID: 40949154756     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja711449e     Document Type: Article
Times cited : (179)

References (25)
  • 13
    • 0043274737 scopus 로고    scopus 로고
    • For use of aryl mesylates as partners in cross-coupling reactions see: a
    • For use of aryl mesylates as partners in cross-coupling reactions see: (a) Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531.
    • (1996) Tetrahedron Lett , vol.37 , pp. 8531
    • Kobayashi, Y.1    Mizojiri, R.2
  • 23
    • 40949089148 scopus 로고    scopus 로고
    • Available from Nippon Chemical Co. (catalogue no. 103099-52-1).
    • Available from Nippon Chemical Co. (catalogue no. 103099-52-1).
  • 24
    • 40949109064 scopus 로고    scopus 로고
    • See Supporting Information for details of butoxyesterification of 4-t- butylphenyltosylate with other bases and solvents
    • See Supporting Information for details of butoxyesterification of 4-t- butylphenyltosylate with other bases and solvents.
  • 25
    • 0042693206 scopus 로고    scopus 로고
    • Substrates with certain electron-withdrawing groups (e.g., 3-cyanophenyl methanesulfonate) were transformed into mixtures of butyl ether and ester when the reaction was carried out in DMSO. Ether formation occurred without ligand and Pd in DMSO presumably via a base-mediated sulfonyl transfer mechanism: sulfonyl transfer occurs to form primary sulfonate and phenol, and phenol displaces primary sulfonate in the presence of base. This has been observed previously: Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11253. This transformation was completely suppressed when the reaction was conducted in toluene or dioxane at 100°C.
    • Substrates with certain electron-withdrawing groups (e.g., 3-cyanophenyl methanesulfonate) were transformed into mixtures of butyl ether and ester when the reaction was carried out in DMSO. Ether formation occurred without ligand and Pd in DMSO presumably via a base-mediated sulfonyl transfer mechanism: sulfonyl transfer occurs to form primary sulfonate and phenol, and phenol displaces primary sulfonate in the presence of base. This has been observed previously: Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11253. This transformation was completely suppressed when the reaction was conducted in toluene or dioxane at 100°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.