Development of Reductive Alkylation Reactions Catalyzed by Newly Designed PSiP Pincer-type Metal Complexes

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PSiP Pincer-type palladium complex-catalyzed hydrocarboxylation of unsaturated hydrocarbons, such as allenes and easily available 1,3-dienes, with carbon dioxide was successfully developed. Treatment of allenes and dienes with 1-5 mol% of silyl pincer-type palladium complex and AlEt_3 or ZnEt_2 as a stoichiometric reductant in DMF under 1 atm CO_2 afforded synthetically useful β,γ-unsaturated carboxylic acids in high yield with high regioselectivity. This protocol is successfully applied to a variety of substrates containing a functional group such as ester, carbamate, ketone and alkene, showing high synthetic utility of this protocol for the synthesis of β,γ-unsaturated carboxylic acids.