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A NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported. This protocol provides an efficient access for highly congested quaternatry carbon centers construction. It also features operationally simplicity, mild reaction conditions and good functional group tolerance. Moreover, the reported procedure can be easily emplified to 1 g scale. Mechanism study reveals the dearomative transformation possibly undergoes a single electron transfer process with NHC radical cation as a reactive intermediate.
Liu et al. (Tue,) studied this question.