Conjugated Nitroolefins as Twofold Electrophiles for the Assembly of Five-Membered Monoheterocycles via MIRC [3+2] Annulation: An Update on Synthetic and Mechanistic Aspects
Lara Bianchi, Massimo Maccagno, Giovanni Petrillo, Cinzia Tavani
TL;DR
This paper reviews the use of conjugated nitroolefins in a specific chemical reaction to build five-membered rings, which are important structures in chemistry.
Contribution
The paper provides an updated review of synthetic and mechanistic aspects of using conjugated nitroolefins in [3+2] annulation reactions over the last decade.
Findings
Conjugated nitroolefins act as twofold electrophiles in [3+2] MIRC annulations.
The methodology is practical and environmentally favorable for synthesizing five-membered monoheterocycles.
The review covers developments in the field from 2015 to 2025.
Abstract
Five-membered monoheterocycles, either isolated or embedded in more complex systems, are ubiquitous structural motifs in nature and hence privileged targets of synthetic chemistry. Among a plethora of methodologies used for their assembly, [3+2] annulation strategies keep attracting particular interest among chemists, partly because of some significant characteristics from both the operative and the environmental viewpoints. Herein, the extensive use of conjugated nitroolefins as twofold electrophilic, two-carbon components of [3+2] MIRC (Michael-Initiated Ring Closure) annulations is reviewed as a practical and mechanistic update covering the last decade (2015–2025).
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Taxonomy
TopicsSynthesis of heterocyclic compounds · Catalytic C–H Functionalization Methods · Catalytic Cross-Coupling Reactions