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Direct coupling of arylacetonitriles and primary alcohols to alpha-alkylated arylacetamides with complete atom economy catalyzed by a rhodium complex-triphenylphosphine- potassium hydroxide system
A direct synthesis of alpha-alkylated arylacetamides from arylacetonitriles and primary alcohols has been accomplished for the first time. In the presence of the rhodium complex [Rh(cod)Cl]2/triphenylphosphine/potassium hydroxide system, the desired alpha-alkylated arylacetamides were obtained in 74-92% yield under microwave conditions. The experimental results in this paper are in sharp contrast with previous reports, where the coupling of arylacetonitriles and primary alcohols produced the alpha-alkylated arylacetonitriles. Mechanistic investigations show that arylacetonitriles are first alpha-alkylated with primary alcohols to produce alpha-alkylated arylacetonitriles, which are further hydrated with the water resulting from the alpha-alkylation step to produce alpha-alkylated arylacetamides. More importantly, this research shows the potential of developing completely atom-economical reactions that involve the hydrogen autotransfer (or hydrogen borrowing) process.
Direct coupling of arylacetonitriles and primary alcohols to alpha-alkylated arylacetamides with complete atom economy catalyzed by a rhodium complex-triphenylphosphine- potassium hydroxide system
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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion