Palladium-catalyzed phenoxycarbonylation of aryl iodides: electronic effect of the substituents on phenol

✍ Scribed by Tetsuya Satoh; Masahiro Ikeda; Masahiro Miura; Masakatsu Nomura

• Book ID: 103997680
• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 597 KB
• Volume: 111
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/1381-1169(96)00071-4

✦ Synopsis

Carbonylation of 4-iodotoluene in the presence of a series of 3-or 4-substituted phenols as nucleophiles using a catalytic amount of PdCl,(PPh,), and tributylamine as base to give aryl 4-methylbenzoates has been carried out. It was found that both electron-withdrawing and donating substituents on phenol enhance the reaction, while the latter ones are relatively more influential. Similar substituent electronic effects were also observed in the stoichiometric reaction of 4-methylbenzoylpalladium complex, trans-4-MeC,H,COPdI(PPh,),, which may correspond to the key intermediate in the catalytic reaction, with the phenols.