Synthesis of β-Phenethyl Ethers by Base-Catalyzed Alcohol Addition Reactions to Aryl Alkenes

Abstract

The direct anti-Markovnikov addition of alcohols to styrene derivatives represents a streamlined route to β-phenethyl ethers, a substructure frequently found in pharmaceuticals and other bioactive ­molecules. Here, we discuss how the development of such a reaction can complement and address limitations of current methods for β-phenethyl ether synthesis. In particular, we highlight our recent ­approach toward achieving this challenging alcohol addition reaction through P₄-t-Bu superbase catalysis. A summary of compatible aryl alkenes and alcohols is provided to inform readers of potential applications of this new catalytic transformation, as well as its current limitations and future directions.

1 Introduction

2 Anti-Markovnikov Alcohol Addition to Aryl Alkenes: Background

3 Superbase-Catalyzed Alcohol Addition to Aryl Alkenes

4 Summary and Outlook

Key words

phosphazene superbases - Brønsted base catalysis - anti-Markovnikov addition - ether synthesis - alcohols - aryl alkenes

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