Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐a]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library.

Stahlberger, Mareen; Schwarz, Noah; Zippel, Christoph; Hohmann, Jens; Nieger, Martin; Hassan, Zahid; Bräse, Stefan

This report describes the synthesis of a [2.2]paracyclophane‐derived annulated 3‐amino‐imidazole ligand library through a Groebke‐Blackburn‐Bienaymé three‐component reaction (GBB‐3CR) approach employing formyl‐cyclophanes in combination with diverse aliphatic and aromatic isocyanides and heteroaromatic amidines. The GBB‐3CR process gives access to skeletally‐diverse cyclophanyl imidazole ligands, namely 3‐amino‐imidazo[1,2‐a]pyridines and imidazo[1,2‐a]pyrazines. Additionally, a one‐pot protocol for the GBB‐3CR by an in situ generation of cyclophanyl isocyanide is demonstrated. The products were analyzed by detailed spectroscopic techniques, and the cyclophanyl imidazo[1,2‐a]pyridine was confirmed unambiguously by single‐crystal X‐Ray crystallography. The cyclophanyl imidazole ligands can be readily transformed to showcase their useful utility in preparing N,C‐palladacycles through regioselective ortho‐palladation.

IMIDAZOLES; HETEROCYCLIC compounds; LIGANDS (Chemistry); X-ray crystallography; AMIDINES; IMIDAZOPYRIDINES; PYRAZINES

Chemistry - A European Journal, 2022, Vol 28, Issue 3, p1

0947-6539

Academic Journal

10.1002/chem.202103511