Synthesis of 1,3-disubstituted-[1.1.1]-bicyclopentane (BCP) salts: arylsulfonium, arylpyridinium and arylammonium isosteres

17 November 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we describe the synthesis of pyridinium, sulfonium and ammonium bicyclo-[1.1.1]-pentane salts as potential aryl isosteres. Arylsulfonium, ammonium and pyridinium salts are central motifs in several natural products, pharmaceuticals, and high value commodities within the industrial chemical sector. The reaction proceeds by a nucleophilic substitution on a bench stable precursor 1,3-diodobicyclo-[1.1.1]-pentane (DIBCP). The transformation displays broad substrate scope, good to excellent yield profile, with several of the BCP products being fully characterised by single crystal X-ray crystallography, highlighting the unique 3-dimensional structure of these potential isosteres. Finally, the pyridinium and quinolinium BCP salts can be cleanly converted into piperidinone and quinolone BCP analogues.

Keywords

Isostere
bicyclo-[1.1.1]-pentane
pyridinium
ammonium
sulfonium

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Experimental procedures, compound characterization, crystallographic data (CCDC 2308434-7) and copies of NMR spectra (PDF)
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.