Ad irect synthesis of a-alkylated arylacetamides from arylacetonitriles andp rimary alcohols has been accomplished for the first time.I nt he presence of the rhodium complex [Rh(cod)Cl] 2 /triphenylphosphine/potassium hydroxide system,t he desired a-alkylated arylacetamides were obtained in 74-92% yield under microwave conditions.T he experimental results in this paper are in sharp contrast with previous reports, where the coupling of arylacetonitriles and primary alcoholsp roduced the a-alkylated arylacetonitriles.M echanistic investigations show that arylacetonitriles are first a-alkylated with primary alcohols to produce a-alkylateda rylacetonitriles, which are further hydrated with the water resulting from the a-alkylation step to produce a-alkylated arylacetamides.M orei mportantly,t his research shows the potentialo fd eveloping completelya tomeconomical reactions that involve the hydrogenautotransfer (or hydrogenborrowing) process.
In the same boat: Tandem rearrangement/N‐alkylation reactions in the presence of a Ru/Ir dual‐catalyst system affords the desired N‐alkylated amines in good‐to‐excellent yields with no intermediate amides or over‐alkylated N,N‐dialkylated amides. This environmentally friendly tandem reaction employs readily available starting materials, affords excellent selectivities for the N‐alkylated amides, and shows high atom efficiency.
Red card for formaldehyde: The direct coupling of indoles with methanol to 3,3'-bisindolylmethanes with good to excellent yields was accomplished by using a commercially available iridium complex. This study demonstrates the potential of direct use of methanol as an alternative to formaldehyde for synthetic transformations.
A novel strategy for the direct synthesis of N-alkylated amides from nitriles, aldoximes and alcohols was proposed and accomplished in the presence of a Cp*Ir complex.
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