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Updated: Dec 28, 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
Methylene C(sp3)-H β,β'-Diarylation of Cyclohexanecarbaldehydes Promoted by a Transient Directing Group and Pyridone
Sahra St John-Campbell1, Andrew J P White1, James A Bull1
1Department of Chemistry, Molecular Sciences Research Hub, Imperial College London,White City Campus, Wood Lane W12 0BZ, U.K.
Abstract:
A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The amide N-substituents are shown to affect yield and can enhance the rate of arylation compared with the α-amino acid. Addition of a pyridone ligand further enhanced reactivity. The reaction is successful for a range of aryl iodides, and various substituted cyclohexane carboxaldehydes, providing functionalized products from simple feedstocks. A mechanism is proposed evoking a transient enamine.
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