Synthesis of Cyclobutanes and Cyclobutenes by Strain-Release-Driven Ring-Opening of Bicyclo[1.1.0]butanes

Dedicated to Professor Hans-Ulrich Reißig on the occasion of his 75^th birthday.

Abstract

Cyclobutanes and cyclobutenes exhibit intriguing structures and demonstrate significant biological activities and diverse synthetic applications. This review aims to summarize recent progress in strain-release-driven ring-opening reactions of bicyclo[1.1.0]butanes (BCBs) to synthesize these four-membered carbon rings. It outlines the strategies, regio- and stereoselectivity, the synthetic scope of reactions, and the mechanistic implications of the catalytic ring-opening process, providing a supplementary perspective to existing reviews.

1 Introduction

2 Thermally Driven Nucleophilic Ring-Opening

3 Thermally Driven Rearrangement and Isomerization Reaction

4 Light-Driven Ring-Opening

5 Transition-Metal/Lewis Acid Catalyzed Ring-Opening

6 Conclusion and Outlook

Key words

strained molecules - bicyclo[1.1.0]butanes - cyclobutanes - cyclobutenes - ring-opening reaction

Publication History

Received: 30 July 2024

Accepted after revision: 23 August 2024

Accepted Manuscript online:
23 August 2024

Article published online:
25 September 2024

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