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Updated: Jul 29, 2025

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Metal-catalysed C-C bond formation at cyclopropanes
Alexis L Gabbey1, Katerina Scotchburn1, Sophie A L Rousseaux2
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, ON, Canada.
Abstract:
Cyclopropanes are important substructures in natural products and pharmaceuticals. Although traditional methods for their incorporation rely on cyclopropanation of an existing scaffold, the advent of transition-metal catalysis has enabled installation of functionalized cyclopropanes using cross-coupling reactions. The unique bonding and structural properties of cyclopropane render it more easily functionalized in transition-metal-catalysed cross-couplings than other C(sp3) substrates. The cyclopropane coupling partner can participate in polar cross-coupling reactions either as a nucleophile (organometallic reagents) or as an electrophile (cyclopropyl halides). More recently, single-electron transformations featuring cyclopropyl radicals have emerged. This Review will provide an overview of transition-metal-catalysed C-C bond formation reactions at cyclopropane, covering both traditional and current strategies, and the benefits and limitations of each.
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