Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols

Professor Jacques Muzart is gratefully acknowledged for his immense contributions to the understanding of the C–O bond cleavage in alcohols.

Abstract

The Suzuki–Miyaura reaction is one of the most powerful tools for the formation of carbon–carbon bonds in organic synthesis. The utilization of alcohols in this powerful reaction is a challenging task. This short review covers progress in the transition-metal-catalyzed Suzuki­–Miyaura-type cross-coupling reaction of π-activated alcohol, such as aryl, benzylic, allylic, propargylic and allenic alcohols, between 2000 and June 2019.

1 Introduction

2 Suzuki–Miyaura Cross-Coupling Reactions of Aryl Alcohols

2.1 One-Pot Reactions with Pre-activation of the C–O Bond

2.1.1 Palladium Catalysis

2.1.2 Nickel Catalysis

2.2 Direct Activation of the C–O Bond

2.2.1 Nickel Catalysis

3 Suzuki–Miyaura-Type Cross-Coupling Reactions of Benzylic Alcohols

4 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allylic Alcohols

4.1 Rhodium Catalysis

4.2 Palladium Catalysis

4.3 Nickel Catalysis

4.4 Stereospecific Reactions

4.5 Stereoselective Reactions

4.6 Domino Reactions

5 Suzuki–Miyaura-Type Cross-Coupling Reactions of Propargylic Alcohols

5.1 Palladium Catalysis

5.2 Rhodium Catalysis

6 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allenic Alcohols

6.1 Palladium Catalysis

6.2 Rhodium Catalysis

7 Conclusions

Key words

C–O bond activation - alcohols - cross-coupling - Suzuki–Miyaura­ - catalysis - green chemistry

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