その他令和8年1月8日
A General Strategy for the Synthesis of Functionalized Cyclopropanes (Abstract & Intro)
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令和8年1月8日
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p.15
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A General Strategy for the Synthesis of Functionalized Cyclopropanes (Abstract & Intro)
令和8年1月8日|p.15
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Supporting Information
ABSTRACT: A general strategy for the synthesis of functionalized cyclopropanes has been developed through a copper-catalyzed three-component reaction of alkynes, diazo compounds, and allylic halides. This protocol features high efficiency, mild conditions, and broad substrate scope.
The development of efficient methods for the construction of cyclopropane rings is of great importance in organic synthesis due to their unique structural features and biological activities. Traditional approaches often suffer from limited substrate scope or harsh reaction conditions. Herein, we report a novel copper-catalyzed three-component reaction that enables the direct assembly of functionalized cyclopropanes from readily available starting materials.
In this study, we explored the reactivity of terminal alkynes with various diazo compounds and allylic halides under copper catalysis. The reaction proceeds smoothly at room temperature, providing the desired cyclopropane products in good to excellent yields. Notably, the method tolerates a wide range of functional groups, including esters, ketones, and heterocycles.
Mechanistic investigations suggest that the reaction involves the formation of a copper-carbene intermediate, which subsequently reacts with the alkyne to generate a vinylcopper species. This intermediate then undergoes nucleophilic substitution with the allylic halide, followed by intramolecular cyclization to afford the cyclopropane product.
The utility of this methodology was further demonstrated by its application in the synthesis of several biologically active compounds. The simplicity and versatility of this approach make it a valuable tool for the construction of complex molecular architectures.
■ INTRODUCTION
Cyclopropanes are ubiquitous motifs in natural products and pharmaceuticals, exhibiting diverse biological activities such as antimicrobial, anticancer, and anti-inflammatory properties. Their strained ring structure also makes them valuable intermediates in organic synthesis, serving as precursors for the construction of more complex molecules.
Despite significant progress in cyclopropane synthesis, many existing methods rely on prefunctionalized substrates or require stoichiometric amounts of metal reagents. Transition-metal-catalyzed reactions have emerged as powerful tools for cyclopropanation, offering improved atom economy and selectivity. However, developing catalytic systems that operate under mild conditions and accommodate a broad range of substrates remains a challenge.
Recently, copper-catalyzed reactions involving diazo compounds have attracted considerable attention due to their ability to generate reactive carbene intermediates under mild conditions. These intermediates can engage in various transformations, including cyclopropanation, C−H insertion, and ylide formation. Building on these advances, we sought to develop a new copper-catalyzed multicomponent reaction for the synthesis of functionalized cyclopropanes.
Herein, we describe a copper-catalyzed three-component reaction of alkynes, diazo compounds, and allylic halides that provides access to a variety of functionalized cyclopropanes. This method offers several advantages, including operational simplicity, mild reaction conditions, and excellent functional group tolerance. Furthermore, the reaction can be performed on a gram scale without significant loss of efficiency.
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