Photoactivated Functionizable Tetracarbonyl(phenylpyridine)manganese(I) Complexes as CO-Releasing Molecules : A Direct Suzuki-Miyaura Cross-Coupling on a Thermally Stable CO-RM

Ward, Jonathan S. and Bray, Joshua T. W. and Aucott, Benjamin J. and Wagner, Conrad and Pridmore, Natalie E. and Whitwood, Adrian C. and Moir, James W. B. and Lynam, Jason M. and Fairlamb, Ian J. S. (2016) Photoactivated Functionizable Tetracarbonyl(phenylpyridine)manganese(I) Complexes as CO-Releasing Molecules : A Direct Suzuki-Miyaura Cross-Coupling on a Thermally Stable CO-RM. European Journal of Inorganic Chemistry, 2016 (31). pp. 5044-5051. ISSN 1434-1948

Abstract

A new class of carbon monoxide-releasing molecules (CO-RMs) are reported based on a previously known tetracarbonyl phenylpyridine manganese(I) motif. A pre-functionalized CO-RM undergoes a direct Pd-catalysed Suzuki–Miyaura cross-coupling with phenylboronic acid to give a π-extended three-ring CO-RM. Cross-coupling conditions were modified to allow coupling of a morpholine-containing boronic acid on to a CO-RM, introducing drug-like functionality. An LED system was used to facilitate controlled CO-release. Irradiation using an LED (400 nm or 365 nm) gives rise to faster CO-release, with lower overall input power than traditional use of a TLC lamp (365 nm), as measured by an assay based on the conversion of deoxymyoglobin to carbonmonoxymyoglobin.