Mild, selective, general method of ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium

David Milstein, J. K. Stille

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Abstract

Benzylchlorobis(triphenylphosphine)palladium(II) catalyzes the reaction of acid chlorides with tetraorganotin compounds to give ketones in quantitative yields. The reaction is general with respect to both reactants, and a wide variety of substituent groups on the acid chloride, including an aldehyde function, is tolerated, thus making this reaction one of the most general methods for ketone synthesis. The reaction is accelerated by oxygen, deactivated by triphenylphosphine, and shows an abnormal dependence on catalyst concentration. Benzoylchlorobis(triphenylphosphine)palladium(II), a key intermediate in the catalytic cycle, has been shown to react with tetramethyltin to afford acetophenone. The mechanism of the catalytic reaction is discussed.

Original languageEnglish
Pages (from-to)1613-1618
Number of pages6
JournalJournal of Organic Chemistry
Volume44
Issue number10
Publication statusPublished - 1979

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ASJC Scopus subject areas

  • Organic Chemistry

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