UC Santa Barbara

Abstract: A new general process for constructing ortho-tert-butyl phenols is presented within the context of other known methods. All are briefly evaluated with regards to regioselectivity, efficiency, and functional group tolerance. In addition, we present an assortment of tert-butyl substrates accessed through o-QM chemistry. Our conclusion is that the o-QM process provides greater yields, flexibility, and generality than most other known methods for delivering ortho-tert-buytlated phenols and their derivatives. 1 Introduction 2 Friedel–Crafts Alkylation 3 Addition of t-Bu– or t-Bu• to Carbonyl Compounds 4 ipso-SNAr Reactions of Aryl Methoxy and tert-Butylsulfoxide Moieties 5 Metal-Mediated Coupling of Aryl Bromides 6 Applications of o-Quinone Methides (o-QMs) 7 Conclusion