Photocatalytic Diheteroarylation of [1.1.1]Propellane for the Construction of 1,3-Diheteroaryl Bicyclo[1.1.1]pentanes

Org Lett. 2024 Nov 1;26(43):9210-9214. doi: 10.1021/acs.orglett.4c03198. Epub 2024 Oct 23.

Abstract

Herein, we report a visible light-induced diheteroarylation reaction of [1.1.1]propellane to synthesize 1,3-diheteroaryl bicyclo[1.1.1]pentanes (BCPs). In this approach, heteroaryl radicals are generated from heteroaryl halides via photocatalysis and subsequently added to [1.1.1]propellane. The in situ generated BCP radicals are then trapped by various heterocycles to furnish 1,3-diheteroaryl BCPs. Notably, this strategy features metal-free, mild conditions and utilizes inexpensive catalyst. For the first time, the diheteroarylation of [1.1.1]propellane could be achieved via a radical strategy, allowing for the efficient synthesis of 1,3-diheteroaryl BCPs with various applications in organic and medicinal chemistry.