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Palladium(II)-catalyzed coupling of allenoic acids and α,β-unsaturated carbonyl compounds through tandem intramolecular oxypalladation and conjugate addition reactions

✍ Scribed by Guosheng Liu; Xiyan Lu


Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
248 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis


A regioselective divalent palladium-catalyzed tandem coupling reaction of allenoic acids with a,b-unsaturated carbonyl compounds was developed. The reaction involves intramolecular oxypalladation of an allene, followed by insertion of the a,b-unsaturated carbonyl compound and protonolysis of the C Pd bond to regenerate the Pd(II) species in the presence of excess halide ions. Functionalized lactones, tetrahydropyranones and dihydropyranones can be synthesized with high regioselectivity in one step.


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## Abstract Rhodium fluoroapatite (RhFAP) is an efficient catalyst for conjugate addition of organoboron reagents to __α__,__β__‐unsaturated carbonyl compounds. A variety of arylboronic acids and __α__,__β__‐unsaturated carbonyl compounds were converted to the corresponding conjugate‐addition produ