Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols

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

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