14072-67-4

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

The invention discloses a method for synthesizing alpha-alkylarylacetamide. In a reaction vessel, aromatic acetonitrile, compound alcohol, a transition metal catalyst metal rhodium complex, alkali, a phosphine ligand and an organic solvent are added; the reaction mixture is subjected to a reaction under a temperature of 130 DEG C in a microwave reactor or under magnetic stirring; the mixture is cooled to room temperature, and is processed through column separation, such that a target compound is obtained. According to the invention, nitrile and alcohol are adopted as initial raw materials; under the participation of the transition metal catalyst, the phosphine ligand and alkali, alpha-alkylarylacetamide is directly synthesized. The reaction has three significant advantages: (1) commercialized or easy-to-prepare nitrile and almost nontoxic alcohol are adopted as initial raw materials; and (2) the reaction has high atomic economy. Therefore, the reaction meets the requirements of green chemistry, and has a good development prospect.

A direct synthesis of α-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 α-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 α-alkylated arylacetonitriles. Mechanistic investigations show that arylacetonitriles are first α-alkylated with primary alcohols to produce α-alkylated arylacetonitriles, which are further hydrated with the water resulting from the α-alkylation step to produce α-alkylated arylacetamides. More importantly, this research shows the potential of developing completely atom-economical reactions that involve the hydrogen autotransfer (or hydrogen borrowing) process.

We describe here an efficient, rapid and selective method for the conversion of nitriles in to their corresponding amides in the presence of PEG-400, aqueous sodium hydroxide system under microwave irradiation.