Regioselective Synthesis of Fused Furans by Decarboxylative Annulation of α,β-Alkenyl Carboxylic Acid with Cyclic Ketone: Synthesis of Di-Heteroaryl Derivatives

Angew Chem Int Ed Engl. 2019 Aug 5;58(32):11039-11043. doi: 10.1002/anie.201906264. Epub 2019 Jul 3.

Abstract

α,β-Alkenyl carboxylic acids undergo CuII -mediated decarboxylative annulation reactions with aliphatic cyclic ketones to provide synthetically valuable di-heterocycles. The annulation process tolerates a variety of aliphatic ketones and heterocyclic alkenyl carboxylic acids, producing substituted fused furan derivatives with complete regioselectivity. The current protocol offers a synthetically applicable pathway to construct a variety of oligo-heterocycles through Cu-mediated single-electron transfer and decarboxylation. Notably, synthesis of relatively inaccessible di-heterocycles has been achieved successfully using this protocol.

Keywords: annulations; copper; heteroarenes; radicals.