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 language | English |
|---|---|
| Pages (from-to) | 1613-1618 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 44 |
| Issue number | 10 |
| Publication status | Published - 1979 |
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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 journal › Article
}
TY - JOUR
T1 - Mild, selective, general method of ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium
AU - Milstein, David
AU - Stille, J. K.
PY - 1979
Y1 - 1979
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=0000268679&partnerID=8YFLogxK
M3 - Article
VL - 44
SP - 1613
EP - 1618
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 10
ER -