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Microbial Biotransformations in the Production and Degradation of Fluorinated Pharmaceuticals
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2020
Cormac D. Murphy, Aoife Phelan
The number of fluorinated drugs has increased steadily from the mid-20th century, and this has reflected the advances in the synthetic methodologies in fluorine chemistry. Given the benefits that fluorine can bring to pharmaceutically active molecules, it is highly likely that the number of fluorinated drugs will continue to increase; in 2017, 8 out of the 29 small molecules approved by the FDA contained fluorine. The widespread inclusion of fluorine in drugs does come with an obvious environmental downside, since there is increasing awareness amongst regulatory bodies and environmental campaigners of the recalcitrance of some fluorinated compounds. Whilst microorganisms might degrade certain fluorinated compounds, for example those that have a fluorophenyl moiety that can be catabolised via established catabolic pathways, others are demonstrably non-biodegradable. In particular, compounds containing the trifluoromethyl group are very common in pharmaceuticals and agrochemicals, and these might be partially degraded to a metabolically dead-end compound, such as trifluoroacetic acid. Thus, it is incumbent that the environmental fate of fluorinated pharmaceuticals is properly investigated, and inevitably this involves assessment of microbial biotransformation, either in pure culture or in a microcosm.
Iodine for vegetable production and livestock breeding
Published in Tatsuo Kaiho, Iodine Made Simple, 2017
Halogens (fluorine, chlorine, bromine, iodine) have played an important role in the development of agricultural chemicals. In particular, chlorine has been widely used as an component of pesticides such as DDT (dichlorodiphenyltrichloroethane) and BHC (benzene hexachloride) (see the diagram). However, the use of chlorine-based agricultural chemicals have been discontinued in developed countries due to safety concerns. In recent years, the introduction of fluorine has shown to significantly change drug efficiency and properties, and the use of fluorine-based agricultural chemicals containing fluorine atoms and the trifluoromethyl group (CF3) have rapidly increased due to their high level of safety. Overall, 30% of all agricultural chemicals presently used are said to be fluorine-based. On the other hand, because iodine is comparatively costly compared to other halogens and in limited supply, hence there are fewer cases of use in agricultural chemicals.
Hydro-trifluoromethyl(thiol)ation of alkenes: a review*
Published in Journal of Sulfur Chemistry, 2022
Seyedeh Bahareh Azimi, Manzarbanou Asnaashariisfahani, Bayan Azizi, Elham Mohammadi, Abdol Ghaffar Ebadi, Esmail Vessally
In this section, we summarize the current literature on the direct hydrotrifluoromethylation reactions of alkenes. These lead to the formation of trifluoromethyl alkanes in a high atom and step economic procedure. For clarity, the reactions will be structured by the type of trifluoromethylating reagents.