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

David Milstein, J. K. Stille

Research output: Contribution to journalArticle

181 Citations (Scopus)

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

Fingerprint

Organotin Compounds
Palladium
Ketones
Chlorides
Acids
Aldehydes
Oxygen
Catalysts
triphenylphosphine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Mild, selective, general method of ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium. / Milstein, David; Stille, J. K.

In: Journal of Organic Chemistry, Vol. 44, No. 10, 1979, p. 1613-1618.

Research output: Contribution to journalArticle

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