α-Arylation of (hetero)aryl ketones in aqueous surfactant media

alpha-Arylation reactions can be performed in water, enabled by a designer surfactant,under mild conditions and in the absence of organic co-solvents. A multitude of aryl and heteroaryl ketones are amenable to coupling with functionalized aryl halides. Use of a lipophilic base that can gain entry to the micellar inner cores mediates enolization. In some cases, palladium loadings as low as 2500 ppm (0.25 mol%) are sufficient for coupling in a completely recyclable medium, exemplifying chemistry in water.

Automated summary

The alpha-arylation reactions can be carried out in water with the help of a designed surfactant, without the need for organic co-solvents, under mild conditions. The enolization is mediated by a lipophilic base that gains entry to the micellar inner cores. Additionally, it is demonstrated that coupling reactions can be efficiently conducted with low palladium loadings in a completely recyclable medium.