2018-Sustainable Industrial Processing Summit
SIPS2018 Volume 2. Amatore Intl. Symp. / on Electrochemistry for Sustainable Development
| Editors: | F. Kongoli, H. Inufasa, M. G. Boutelle , R. Compton, J.-M. Dubois, F. Murad |
| Publisher: | Flogen Star OUTREACH |
| Publication Year: | 2018 |
| Pages: | 216 pages |
| ISBN: | 978-1-987820-84-3 |
| ISSN: | 2291-1227 (Metals and Materials Processing in a Clean Environment Series) |
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Medicinal Electrosynthesis: A Green, Scalable, Economical and Safe Way to Activate Organic and Organometallic Molecules
Kevin Lam1;1THE UNIVERSITY OF GREENWICH, Chatham Maritime, United Kingdom;
Type of Paper: Regular
Id Paper: 77
Topic: 47
Abstract:
Electrosynthesis is a powerful tool in organic chemistry that circumvents the use of expensive and toxic reagents for the generation of reactive intermediates. During electrosynthesis, molecules are activated under mild and green conditions directly at the surface of an electrode. [1] Even though a plethora of transformations have been developed and many of them were successfully used in several industrial processes [2-4], the potential of preparative organic electrochemistry remains largely underestimated. However, the growing impetus to look for greener and cheaper alternatives to classic synthetic methodologies prompted us to further investigate new electrochemical reactions. We have recently developed two new electrochemical methodologies that allow the generation of organic and organometallic radicals under mild, green, economical, and safe conditions.
The first one allowed us to prepare a new class of organometallic drugs based on the cymantrene motif (CpMn(CO)<sub>3</sub>). Anodic oxidation of the metallic core, under weakly coordinating conditions, allowed us to selectively replace one of carbonyl ligand (CO) by another ligand (L). This helped us to finely tune the physical properties of the drug, such as its redox potential or its lipophilicity. The final compounds have revealed to inhibit autophagy, and to have both very promising anticancer and antimalarial properties. [5-7]
In the same vein, we have recently developed a new electrosynthetic methodology to generate aroyloxy and benzamidyl radicals under mild conditions. The electrochemical reaction was even successfully scaled up to a 2g scale. [8] We are planning on using those radicals in the synthesis of other biologically relevant products such as phthalides, [9, 10] dihydroisocoumarins, [11, 12] isoindolinones, [13] and dihydroisoquinolones. [14] Those compounds are known to be important classes of bioactive compounds that are very often found in natural products. Several synthetic strategies have been developed for the synthesis of those scaffolds, but still rely on the use of expensive and hazardous chemicals which would prevent any industrial scale up. [15-17]
Keywords:
Activation of small inert molecules; Drug design; Electrochemistry; Electrosynthetic protocols; Molecular electrochemistry; Organic chemistry; Organometallic chemistry;References:
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