Visible Light‐Mediated Cyclopropanation: Recent Progress

Abstract

Cyclopropanes are one of the most important strained rings existing in various pharmaceutical products and secondary metabolites. They are also widely used in total synthesis of natural products, medicinal chemistry, and materials science. In the past years, photochemical cyclopropanation has been gradually developed as a robust and attractive synthetic method to prepare diverse cyclopropane backbones. In this review, we summarize recent advances in the visible light‐mediated cyclopropane synthesis, especially in photochemical cyclopropanation using carbene transfer strategy and photocatalytic radical cyclopropanation reactions.

Photosensitized O 2 enables intermolecular alkene cyclopropanation by active methylene compounds

“…Because our reaction protocol involves catalytic I 2 , we also investigated other mechanistic possibilities by which photoredox catalysis operates for cyclopropanation with halogenated carbon sources ( 45 ). Photoredox alkene cyclopropanation reactions with halogenated carbon sources have been previously proposed to proceed by atom transfer radical addition (ATRA) ( 46 , 47 ).…”

Cyclopropylcarbinyl cation chemistry in synthetic method development and natural product synthesis: cyclopropane formation and skeletal rearrangement

“…22 To date, numerous cyclopropanation reactions have been developed. [21][22][23][24] The most common approaches involve carbene/carbenoid insertion into olefin (Fig. 1A).…”

Rapid Olefin Cyclopropanation Catalyzed by a Bioinspired Cobalt Complex

“…Cyclopropane is a fundamental building block with unique chemical and physiological properties due to its rigid and strained ring structure. The three‐membered carbocyclic ring scaffold appears widely in natural and synthetical biologically active products and has been adopted in numerous drugs and insecticides [1–8] . Given its importance in medicinal chemistry, the last few decades have witnessed a rapid increase in reports on the preparation of substituted cyclopropanes.…”

“…The three-membered carbocyclic ring scaffold appears widely in natural and synthetical biologically active products and has been adopted in numerous drugs and insecticides. [1][2][3][4][5][6][7][8] Given its importance in medicinal chemistry, the last few decades have witnessed a rapid increase in reports on the preparation of substituted cyclopropanes. Among the methods available for the synthesis of cyclopropanes, transition-metal-catalyzed cyclopropanation of olefins with diazo compounds offers the most robust and atom-efficient approach.…”