Silicone as an Organosilicon Reagent 2. Rhodium-catalyzed Conjugate Addition of the Silicone Reagent to α,β-Unsaturated Carbonyl Compounds

Abstract

The reaction of poly(phenylmethylsiloxane) with α,β-unsaturated carbonyl compounds in the presence of aqueous K₂CO₃ and 3 mol% of [Rh(OH)(cod)]₂ gives 1,4-conjugate addition product in good yields. Arylchlorosilanes also undergo the conjugate addition in excellent yields under similar conditions.

silicone - rhodium complex - conjugate addition - potassium carbonate - arylchlorosilanes

References

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<A NAME="RY23301ST-2">2</A>

Available from Chisso Chemicals Co. Ltd.; MW = 2500-2700. We thank Chisso Chemicals Co. Ltd. for kind donation of silicone reagents.

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Although we described that the reaction of silanediol with β-substituted substrates did not occur (ref. [4] ) under the reported conditions, further optimization revealed to undergo the conjugate addition of such substrates with silanediol recently. These results will be described in due course.

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All products were identical with authentic samples.