A continuous flow synthesis of [1.1.1]propellane and bicyclo[1.1.1]pentane derivatives

Kian Donnelly; Marcus Baumann

doi:10.1039/d0cc08124h

A continuous flow synthesis of [1.1.1]propellane and bicyclo[1.1.1]pentane derivatives

Chem Commun (Camb). 2021 Mar 18;57(23):2871-2874. doi: 10.1039/d0cc08124h.

Authors

Kian Donnelly¹, Marcus Baumann¹

Affiliation

¹ School of Chemistry, University College Dublin, Science Centre South, Belfield, D04 N2E2, Ireland. marcus.baumann@ucd.ie.

PMID: 33616143
DOI: 10.1039/d0cc08124h

Abstract

A continuous flow process to generate [1.1.1]propellane on demand is presented rendering solutions of [1.1.1]propellane that can directly be derivatised into various bicyclo[1.1.1]pentane (BCP) species. This was realised in throughputs up to 8.5 mmol h-1 providing an attractive and straightforward access to gram quantities of selected BCP building blocks. Lastly, a continuous photochemical transformation of [1.1.1]propellane into valuable BCPs bearing mixed ester/acyl chloride moieties was developed.