Copper(I)-Mediated 11C-Carboxylation of (Hetero)arylstannanes

Ian R Duffy; Neil Vasdev; Kenneth Dahl

doi:10.1021/acsomega.0c00524

Copper(I)-Mediated ¹¹C-Carboxylation of (Hetero)arylstannanes

ACS Omega. 2020 Apr 2;5(14):8242-8250. doi: 10.1021/acsomega.0c00524. eCollection 2020 Apr 14.

Authors

Ian R Duffy¹, Neil Vasdev^{1

2}, Kenneth Dahl¹

Affiliations

¹ Azrieli Centre for Neuro-Radiochemistry, Brain Health Imaging Centre, Centre for Addiction and Mental Health, 250 College Street, Toronto, ON M5T 1R8, Canada.
² Department of Psychiatry, University of Toronto, 250 College Street, Toronto, ON M5T 1R8, Canada.

Abstract

A novel copper-mediated carboxylation strategy of aryl- and heteroaryl-stannanes is described. The method serves as a mild (i.e., 1 atm) carboxylation method using stable carbon dioxide and is transferable as a radiosynthetic approach for carbon-11-labeled aromatic and heteroaromatic carboxylic acids using sub-stoichiometric quantities of [¹¹C]CO₂. The methodology was applied to the radiosynthesis of the retinoid X receptor agonist, [¹¹C]bexarotene, with a decay-corrected radiochemical yield of 32 ± 5% and molar activity of 38 ± 23 GBq/μmol (n = 3).