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- Title
A Versatile, Functional Group-Tolerant, and Bench-Stable Iron Precatalyst for Building Arene and Triazine Rings by [2+2+2] Cycloadditions.
- Authors
Parisot, William; Haddad, Mansour; Phansavath, Phannarath; Lefèvre, Guillaume; Ratovelomanana-Vidal, Virginie
- 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 crosscycloisomerization 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.
- Subjects
IRON; CYCLOISOMERIZATION; TRIAZINES; RING formation (Chemistry); CALCIUM cyanamide; ALKYNES
- Publication
Chemistry - A European Journal, 2024, Vol 30, Issue 22, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202400096