Solvent-Dependent Photochemistry for Diverse and Selective C-H Functionalization of 2-tert-Butyl-1,4-Benzoquinones

Abstract

Controlling a reaction to selectively produce a set of distinct valuable compounds from the same substrate is a highly attractive topic in synthetic chemistry. In this work, the solvent-dependent photochemistry of 2-tert-butyl-1,4-benzoquinones to achieve diverse C-H functionalization was investigated, which afforded three selective transformations: (1) intermolecular C-O bond formation in non-fluorinated alcoholic solvents; (2) perfluorinated hexafluoroisopropanol solvent-promoted intramolecular cyclization to afford coumaran derivatives; (3) 1,4-dioxane solvent-induced hydrogen atom transfer to afford 2-methylallyl hydroquinones.