Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols

David Rosa; Andrei Nikolaev; Nisha Nithiy; Arturo Orellana

doi:10.1055/s-0034-1380156

Synlett, Table of Contents

Synlett 2015; 26(04): 441-448
DOI: 10.1055/s-0034-1380156

account

Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols

David Rosa

Department of Chemistry, York University, 4700 Keele Street, Toronto ON, M3J 1P3, Canada Email: aorellan@yorku.ca

,

Andrei Nikolaev

Department of Chemistry, York University, 4700 Keele Street, Toronto ON, M3J 1P3, Canada Email: aorellan@yorku.ca

,

Nisha Nithiy

Department of Chemistry, York University, 4700 Keele Street, Toronto ON, M3J 1P3, Canada Email: aorellan@yorku.ca

,

Arturo Orellana*

Department of Chemistry, York University, 4700 Keele Street, Toronto ON, M3J 1P3, Canada Email: aorellan@yorku.ca

› Author Affiliations

Abstract

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Abstract

Strained alcohols have featured prominently in a wide array of transition-metal-catalyzed cross-coupling reactions, but methods involving cyclopropanols have only been developed relatively recently. In this account, we describe our group’s work in this area, and we provide a concise summary of other palladium-catalyzed methods for C–C bond-forming reactions using cyclopropanols.

1 Introduction

2 Cross-Coupling Reactions Using Strained Tertiary Alcohols

3 Base- or Acid-Mediated Ring-Opening Reactions of Strained Alcohols

4 Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols

4.1 Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols with Aryl Halides

4.2 Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols with Benzyl Halides

4.3 Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols with Acyl Halides

4.4 Direct Arylation Using Cyclopropanol-Derived Palladium Homoenolates

4.5 Synthesis of Quinolines from Cyclopropanols

5 Conclusions

Key words

palladium - cross-coupling - cyclopropanols - strain - C–C cleavage - homoenolates

Full Text

References

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