Heck Reaction of Baylis–Hillman Adducts with Iodobenzenes Using a Catalytic Amount of Pd/C under Solvent-Free Conditions

Abstract

The reaction of Baylis–Hillman adducts with iodobenzenes using commercially available palladium-on-carbon as a catalyst under solvent-free conditions afforded the corresponding coupling products, α-benzyl-β-keto esters, in high to excellent yields. The reactions are very efficient.

Key words

Baylis–Hillman adduct - Heck reaction - palladium-on-carbon - iodobenzenes - α-benzyl-β-keto esters

• References

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• 21 CAS registry number of the reported products: 3a: 56409-75-7 (ethyl 2-benzyl-3-oxo-3-phenylpropanoate), 3b: 1190081-72-1 [ethyl 2-benzyl-3-(4-nitrophenyl)-3-oxo-propanoate], 3c: 776297-03-1 [ethyl 2-benzyl-3-(4-chloro-phenyl)-3-oxopropanoate], 3d: 1195307-73-3 (ethyl 2-benzyl-3-(4-methylphenyl)-3-oxopropanoate), 3e: 1190081-70-9 [ethyl 2-benzyl-3-(4-methoxyphenyl)-3-oxopropanoate], 3f: 1190081-73-2 [ethyl 3-(1,3-benzo­-dioxol-5-yl)-2-benzyl-3-oxopropanoate], 3g: 776297-00-8 [ethyl 2-benzyl-3-(furan-2-yl)-3-oxopropanoate], 3h: 776297-01-9 [ethyl 2-benzyl-3-oxo-3-(thiophen-2-yl)pro-panoate], 3i: 534599-79-6 (ethyl 2-benzyl-3-oxopen-tanoate), 3j: 167547-59-3 [ethyl 2-(4-methoxybenzyl)-3-oxo-3-phenylpropanoate], 3k: 867214-92-4 [ethyl 2-(3-methoxybenzyl)-3-oxo-3-phenylpropanoate], 3l: 859189-00-7 [ethyl 2-(4-methylbenzyl)-3-oxo-3-phenylpropanoate], 3m: 107520-73-0 [ethyl 2-(4-nitrobenzyl)-3-oxo-3-phenylpropanoate], 3n: 859189-07-4 [ethyl 2-(4-chlorobenzyl)-3-oxo-3-phenylpropanoate]
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