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

Sunisa Akkarasamiyo; Somsak Ruchirawat; Poonsaksi Ploypradith; Joseph S. M. Samec

doi:10.1055/s-0039-1690740

Synthesis, Table of Contents

Synthesis 2020; 52(05): 645-659
DOI: 10.1055/s-0039-1690740

short review

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

Sunisa Akkarasamiyo

^aDepartment of Organic Chemistry, Stockholm University, 106 91 Stockholm, Sweden Email: Joseph.samec@su.se

^cLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand

,

Somsak Ruchirawat∗

^bProgram in Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, 906 Kamphaeng Phet 6 Road, Talat Bang Khen, Laksi, Bangkok 10210, Thailand

^cLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand

,

Poonsaksi Ploypradith∗

^bProgram in Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, 906 Kamphaeng Phet 6 Road, Talat Bang Khen, Laksi, Bangkok 10210, Thailand

^cLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand

,

Joseph S. M. Samec∗

^aDepartment of Organic Chemistry, Stockholm University, 106 91 Stockholm, Sweden Email: Joseph.samec@su.se

› Author Affiliations

Abstract

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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

Full Text

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