Multicomponent Radical Cross‐Coupling Reaction of [1.1.1]Propellane: Synthesis of 1‐Arylthiol‐3‐Heteroaryl Bicyclo[1.1.1]pentanes †

Abstract

Herein, a visible light‐mediated multicomponent radical cross‐coupling reaction of [1.1.1]propellane with N‐heterocycles and disulfides is described. The mild conditions enabled the installation of the BCP motif in a wide variety of compounds in the absence of photocatalyst, additive and metal catalyst, with excellent functional group tolerance, This methodology opens a approach for the synthesis of potentially bioactive 1‐arylthiol‐3‐heteroaryl bicyclo[1.1.1]pentanes in moderate to good yield.

Visible photons as ideal reagents for the activation of coloured organic compounds

“…The photocleavage of a PhS–SPh bond was used for a multicomponent radical cross-coupling reaction initiated with the sulfur radical addition onto [1.1.1]propellane that, in the presence of N-heterocycles, formed potentially bioactive 1-arylthiol-3-heteroaryl bicyclo[1.1.1]pentanes. 173…”

“…172 The photocleavage of a PhS-SPh bond was used for a multicomponent radical cross-coupling reaction initiated with the sulfur radical addition onto [1.1.1]propellane that, in the presence of N-heterocycles, formed potentially bioactive 1-arylthiol-3-heteroaryl bicyclo[1.1.1]pentanes. 173 The direct cleavage of an S-H bond to generate a thiyl radical in the presence of an alkene (or an alkyne) is quite common under UV irradiation to perform the so-called thiolene (or a thiol-yne) reaction. [174][175][176] In rare instances, the reaction may be promoted by visible-light as depicted in Scheme 41.…”

Metal and catalyst-free strategy to access 1,3-thio-heteroaryl BCP derivatives

“…While our manuscript was under preparation, the Jirong Wu group published similar results. 11 Our methodology is extended to synthesize 2 H -indazole derived heterocycles that are widely employed in medicinal chemistry and materials research.…”