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Volumn , Issue 12, 2002, Pages 1976-1982

Regioselective synthesis of 4-substituted-1-aryl-1-butanones using a Sonogashira-hydration strategy: Copper-free palladium-catalyzed reaction of terminal alkynes with aryl bromides

Author keywords

1 aryl 1 butanones; 3 butyn 1 ol; Aryl bromide; Hydration; Palladium catalyst

Indexed keywords

ACID; ALCOHOL DERIVATIVE; ALKANONE; ALKYNE; BROMIDE; COPPER; N,N DIMETHYLFORMAMIDE; OXYGEN; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 0036456054     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35587     Document Type: Article
Times cited : (85)

References (77)
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    • note
    • Dimerization of terminal alkyne in the presence of copper(I) salt and amine base is a required process for the in situ conversion of Pd(II) to the active catalyst Pd(0), see ref. 16a.
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    • Note
    • +].
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    • note
    • (a) Palladium metal deposited on the wall of the reaction flask perhaps did not participate in the hydration step. (b) The alkyne was purified carefully using column chromatography in order to ensure the removal of the traces amount of Pd-catalyst.
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    • See also ref. 26
    • For hydration of alkynes controlled by neighboring group participation, see: (a) Stork, G.; Borch, R. J. Am. Chem. Soc. 1964, 86, 935. (b) Hooz, J.; Layton, R. B. Can. J. Chem. 1970, 50, 1105; See also ref. 26.
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    • O-Formylation of alcohols using DMF in the presence of other reagents has been reported, see for example: (a) Barluenga, J.; Campos, P. J.; Gonzalez-Nunez, E.: Asensio, G. Synthesis 1985, 426. (b) Luca, L. D.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 5152.
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    • O-Formylation of alcohols using DMF in the presence of other reagents has been reported, see for example: (a) Barluenga, J.; Campos, P. J.; Gonzalez-Nunez, E.: Asensio, G. Synthesis 1985, 426. (b) Luca, L. D.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 5152.
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