B(C6F5)3-Catalyzed [2+3]-Cyclative o,m-diC-H Functionalization of Phenols

Metal-free catalytic C-H functionalization is highly desired for the construction of C-C bonds. We herein report a highly chemoselective consecutive C-H [2+3]-cyclative functionalization for the simultaneous formation of two C-C bonds with construction of polycyclic phenols catalyzed by commercially available and low-cost B(C6F5)(3). This catalytic system tolerates a wide range of substrate scope, providing a series of 2,6,7,8-tetrahydroacenaphthylen-3-ol-type polycyclic compounds efficiently. Several derivatizations of the catalytic products have also been conducted to show the potential application of this method in synthesis of polycyclic compounds.

Automated summary

We report a highly chemoselective consecutive C-H [2+3]-cyclative functionalization for the simultaneous formation of two C-C bonds, constructing polycyclic phenols without the use of metal catalyst. The catalytic system, using commercially available and low-cost B(C6F5)(3), tolerates a wide range of substrates and efficiently produces 2,6,7,8-tetrahydroacenaphthylen-3-ol-type polycyclic compounds. Additionally, several derivative reactions of the catalytic products demonstrate the potential application of this method in the synthesis of polycyclic compounds.