B(C6 F5 )3 -Catalyzed [2+3]-Cyclative o,m-diC-H Functionalization of Phenols

Chemistry. 2023 Dec 19;29(71):e202301595. doi: 10.1002/chem.202301595. Epub 2023 Nov 5.

Abstract

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(C6 F5 )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.

Keywords: B(C6F5)3; C−H functionalization; [2+3] cyclization; phenols; polycyclic compounds.