Preparation of benzolactams by Pd(OAC)2-catalyzed direct aromatic carbonylation

Journal of the American Chemical Society

Volumn 126, Issue 44, 2004, Pages 14342-14343

  Orito, Kazuhiko ^a   Horibata, Akiyoshi ^a   Nakamura, Takatoshi ^a   Ushito, Harumi ^a   Nagasaki, Hideo ^a   Yuguchi, Motoki ^a   Yamashita, Satoshi ^a   Tokuda, Masao ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; AMINE; ARALKYLAMINE; AROMATIC COMPOUND; BENZENE DERIVATIVE; BENZOLACTAM DERIVATIVE; BENZOLACTONE DERIVATIVE; CARBON MONOXIDE; COPPER DERIVATIVE; LACTAM DERIVATIVE; LACTONE DERIVATIVE; NITROGEN; PALLADIUM; PHOSPHINE; TOLUENE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; GAS; ISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; THIN LAYER CHROMATOGRAPHY;

EID: 7744224233     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045342+     Document Type: Article

References (25)

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12. Carbonylation of primary amines, including benzylicamines or phenethylamines, under the same conditions, produced no benzolactams but produced ureas in good yields. The details will be reported elsewhere.
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19. 2O.
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24. Benzolactam 2d was probably formed via a halogen-metal exchange with a Pd(0) catalyst generated in situ.
25. It should be noted that carbonylation of the hydrochloride of phenethylamine 1c at 20 atm of CO afforded benzolactam 3c in 79% yield, probably as a result of an electrophilic aromatic carbonyation.