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This is a Experimental Study study.

October 2, 2025

Synthesis of Densely Functionalized Pyrroles via Photoinduced C-Insertion into N-Alkylenamines: Sequential C(sp2)–H/C(sp3)–H Activation with Bromine Radicals

Puntos clave

This method enables the efficient synthesis of densely functionalized pyrroles through a novel triple-cleavage process.
The use of triethylamine as a halogen bonding acceptor facilitates the key Csp3–Br bond homolysis step during the cyclization.
Bromine radicals play a dual role, coactivating N-alkylenamines and enabling the formation of target heterocycles.
The reaction features readily available starting materials like alkyl amines, allowing for greater accessibility in synthetic applications.

Resumen

Photoinduced Csp3–Br bond homolysis of ArCOCF2Br using triethylamine as the halogen bonding (XB) acceptor was a key step for the 2 + 2 + 1 cyclization. An unprecedented strategy for assembling privileged pyrroles and their fused scaffolds via metal-, oxidant-free C-incorporation into N-alkylenamines through a triple-cleavage process has been disclosed. This method uses readily available alkyl amines, alkynes, or CF3-containing N-benzylenamines as the starting material and features two consecutive C–C-forming reactions with ArCOCF2Br as the carbon source. The transformation exploits the dual reactivity of bromine radicals─hydrogen-atom transfer (HAT) and reversible radical addition (RRA)─to coactivate the N-alkylenamines, and the resulting open-shell intermediates are then intercepted by in situ-generated difluoroalkyl radicals to deliver the target heterocycles.

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