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Updated: Jul 4, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
A Versatile, Functional Group-Tolerant, and Bench-Stable Iron Precatalyst for Building Arene and Triazine Rings by
William Parisot1, Mansour Haddad1, Phannarath Phansavath1
1PSL University, Chimie ParisTech, CNRS UMR 8060, Institute of Chemistry for Life and Health Sciences, CSB2D Team, 75005, Paris, France.
Abstract:
We report an efficient iron-catalyzed cycloaddition procedure leading to the construction of (hetero)aromatic rings by alkyne [2+2+2] cycloisomerization. This method relies on the use of an air-stable (N,N)Fe(II) precursor easily prepared from a commercially available ligand derived from 1,10-phenanthroline, reduced in situ into a catalytically active non-innocent (N,N ⋅-)2Fe(II) species. This system displays a large scope application, operates under mild conditions and at low catalytic charges (25 cycloadducts formed, up to 1.5 mol% catalyst). Moreover, this method also enables access to 29 cycloadducts by cross-cycloisomerization between 1,6- or 1,7-diynes and alkynes in near-equimolar conditions. 1,3,5-Triazines can also be prepared with this procedure starting from the corresponding cyanamides. Scale-up reactions and post-functionalization of several cycloadducts also show that this [2+2+2] cycloaddition can be used in multistep sequences.
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