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Synthesis

C–H And C–C Bond Activations Join Hands

Separate activation reactions and electrophilic addition are combined in a single process

by Stu Borman
December 16, 2013 | A version of this story appeared in Volume 91, Issue 50

C –H bonds can be activated selectively to convert them to C–C and C-heteroatom bonds, and C–C bonds can be activated selectively to convert them to C–H, C–Si, and other bonds, but these techniques have been carried out separately. Combining them could aid the synthesis of complex organic compounds. Now, Ilan Marek of Technion, in Haifa, Israel, and coworkers find that a zirconium-based reagent reacts with cyclopropane-containing substrates with single chiral centers to combine in a single process allylic C–H activation, selective C–C bond activation, and selective functionalization with two different electrophiles (Nature 2013, DOI: 10.1038/nature12761). The process opens the cyclopropane ring, and the resulting acyclic products each have two chiral centers, including the substrate’s original chiral center. “This work emphasizes the feasibility of synthetic approaches to exploit the multifold reactivity of a single substrate … by combining transformations that are otherwise difficult to perform,” the researchers note.

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