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

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...

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Bibliographic Details
Published in:European journal of inorganic chemistry 2016-11, Vol.2016 (31), p.5044-5051
Main Authors: Ward, Jonathan S., Bray, Joshua T. W., Aucott, Benjamin J., Wagner, Conrad, Pridmore, Natalie E., Whitwood, Adrian C., Moir, James W. B., Lynam, Jason M., Fairlamb, Ian J. S.
Format: Article
Language:English
Subjects:
Carbon
Carbon monoxide
Chemical reactions
Control systems
Conversion
Coupling (molecular)
Cross coupling
Irradiation
Lamps
Manganese
Photochemistry
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Summary: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. Photoactivated CO‐releasing molecules have been traditionally irradiated using a TLC lamp. In this paper the use of LEDs close to the sample is reported. This gives efficient CO release compared to a TLC lamp. The complex shown releases CO efficiently and can be functionalised further with a Suzuki reaction.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.201600775