Organocatalytic Direct Csp³−H Difluoroalkylation of N‐Aryltetrahydroisoquinoline

We describe herein the catalytic strategy to generate difluoroenolates from difluoroisoxazolacetophenone (DFIO) for C─C bond formation, allowing for the development of the organocatalytic difluoroalkylation of N ‐aryl tetrahydroisoquinoline. The reaction is performed in the absence of chemical oxidants under mild conditions and only requires organic base as a catalyst and molecular oxygen as an oxidant. In addition, this protocol provides a new and convenient approach for the synthesis of compounds containing α , α ‐difluoroketone motif.