Photoinduced Efficient Catalytic -Alkylation Reactions of Active Methylene and Methine Compounds with Nonactivated Alkenes

In catalytic alpha-alkylation reactions of carbonyl compounds, although S(N)2-type substitution reactions of enolates with alkyl halides are a conventional methodology, addition reactions with alkenes are more desirable because of their atom-economical character; however, reactions with nonactivated alkenes are challenging. Here, we developed highly efficient catalytic alpha-alkylation reactions of active methylene and methine compounds with nonactivated alkenes such as 1-decene using an organophotocatalyst and lithium thiophenoxide as a Lewis acid/Bronsted base/hydrogen atom transfer (HAT) multifunctional catalyst under blue-light irradiation. The reaction was also performed with a higher degree of efficiency under a continuous-flow system to obtain the products in multigram scales. The present reaction system enables highly efficient and practical alpha-alkylation reactions of active methylene and methine compounds to be achieved.