Synthesis of 2-(Diarylmethylene)-3-benzofuranones Promoted via Palladium-Catalyzed Reactions of Aryl iodides with 3-Aryl-1-(2- tert-butyldimethyl­silyloxy)phenyl-2-propyn-1-ones

Abstract

3-Substituted-1-(2-tert-butyldimethylsilyloxy)phenyl-2-propyn-1-ones were coupled with aryl iodides by using palladium as a catalyst in ambient MeOH solution and gave 2-(diarylmethylene)-3-benzofuranones in moderate to good yields.

palladium - coupling - cyclizations

References

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7

Treatment of 2-hydroxybenzaldehyde with TBDMSCl and imidazole gave compound 6 in 95% yield. Applying phenylacetylene with n-BuLi in THF resulted a respective lithium salt. Subsequent exposure the aldehyde 6 to the lithium salt provided the alcohol 7a in 90% yield. The α,β-unsaturated ketone 1a was obtained by oxidation of 7a with MnO₂ in 90% yield.