Recent Advances in Direct Catalytic Dehydrative Substitution of Alcohols

Abstract

This review describes methods for the direct catalytic dehydrative substitution of alcohols in the absence of stoichiometric activating agents, excluding methods that involve transfer hydrogenation. Although some earlier literature is discussed, this review mainly covers literature published from 2010 through August 2015.

1 Introduction

2 S_N1-Type Reactivity

2.1 π-Activated Alcohols

2.1.1 Benzylic Alcohols

2.1.2 Allylic Alcohols

2.1.3 Propargylic Alcohols

2.2 Aliphatic Alcohols

2.3 Chemoselectivity Considerations

3 Stereospecific Methods

4 Enantioselective Methods

4.1 Enantioinduction via Transient Chiral Nucleophiles

4.1.1 Nucleophilic Capture of Cationic Intermediates

4.1.2 Nucleophilic Capture of Transition-Metal-Stabilized Intermediates

4.2 Enantioinduction via Transient Chiral Nucleophiles

4.3 Enantioinduction via Synergistic Chiral Catalysis

4.4 Enantioinduction via Bifunctional Catalysis

5 Conclusion and Outlook

Key words

dehydrative substitution - carbocations - homogeneous catalysis - asymmetric catalysis

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