Metal-free oxidative formal C(sp2)-H arylation of cyclopentene-1,3-diones with β-naphthols

An efficient, mild, and transition-metal free formal C(sp(2))-H arylation of prochiral 2,2-disubstituted cyclopentene-1,3-diones is reported. This oxidative arylation with beta-naphthols proceeds via base-mediated C-Michael addition followed by aerial oxygen insertion and a subsequent alpha-hydroperoxy elimination sequence. This operationally simple and environmentally benign transformation is highly scalable and does not require any pre-functionalization. Moreover, this reaction affords excellent yields of alpha-substituted beta-naphthols bearing all-carbon quaternary centers.

Automated summary

An efficient and mild transition-metal free formal C(sp(2))-H arylation method is reported, which does not require pre-functionalization and is environmentally friendly with high yield.