Synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines via halosulfoamidation of [1.1.1]propellane with sodium hypohalites and sulfonamides

Abstract

Herein, we report a catalyst-free synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines under mild conditions. The reaction involves the use of sodium hypohalites and sulfonamides to generate N-halosulfonamides in situ, which subsequently...

Synthesis of Bicyclo[1.1.1]pentane Carboxamides and Ketones from [1.1.1]Propellane

“…However, extensive literature survey shows that these methods are mainly focused on BCP amines and BCP aryls. [11][12][13][14][15][16][17][18] By comparison, the synthesis of monosubstituted BCP carboxamides is very limited, especially through the direct addition of [1.1.1]propellane. For example, Taylor group [19] and Hossain [20] group have reported a multi-step way to access monosubstituted BCP carboxamides via the formation of BCP carboxylic acid, respectively (Scheme 1, A).…”

Visible light-induced synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane ketonesviacooperative photoredox and N-heterocyclic carbene catalysis

“…Inspired by our general interest in [1.1.1]propellane 19 and radical chemistry, 20 herein we report a cooperative NHC and iridium dual-catalyzed three-component reaction for the construction of 3-benzoylbicyclo[1.1.1]pentane-1-acetates. In this strategy, diazo esters were selected as primary radical precursors as these only produce N 2 as a by-product while generating the corresponding radical species through a photocatalytic proton-coupled electron transfer (PCET) process.…”

Photocatalyzed 1,3-Bromodifluoroallylation of [1.1.1]Propellane with α-Trifluoromethylalkenes and KBr Salts

“…Very recently, the Jiang group demonstrated a visible-light driven synthesis of 1brominated-3-sulfonylamino BCPs, where a N-centered radical addition to [1.1.1]propellane is involved. 13 As of the current state, the synthesis of 1-brominated-3-substituted BCPs via the addition of bromine radicals to [1. 1.1]propellane has yet to be reported.…”