Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water

Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water

Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic acids in good yields. Water may play important...

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Veröffentlicht in:Organic letters 2011-12, Vol.13 (24), p.6512-6515
Hauptverfasser: Hikawa, Hidemasa, Yokoyama, Yuusaku
Format: Artikel
Sprache:eng
Schlagworte:
Benzyl Alcohols - chemistry
Catalysis
Chemistry, Organic - methods
Molecular Structure
ortho-Aminobenzoates - chemistry
Palladium - chemistry
Water - chemistry
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Zusammenfassung:Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic acids in good yields. Water may play important roles for the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2028042