The first photoredox-catalyzed defluoroborylation of polyfluoroarenes with NHC-BH has been facilely achieved at room temperature via a single-electron-transfer (SET)/radical addition pathway. This new strategy makes full use of the advantage of photoredox catalysis to generate the key boryl radical via direct activation of a B-H bond. Good functional group tolerance and high regioselectivity offer this protocol incomparable advantages in preparing a wide array of valuable polyfluoroarylboron compounds. Moreover, both computational and experimental studies were performed to illustrate the reaction mechanism.
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http://dx.doi.org/10.1021/acs.orglett.0c00020 | DOI Listing |
Org Lett
December 2024
College of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), 266580 Qingdao, P. R. China.
To provide fluorinated allylamines, a visible-light photocatalytic C-F/C-H coupling of easily accessible -difluoroalkenes and secondary -alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility and a broad scope including complex natural product derivatives, thus providing a green method for the preparation of high-value functionalized monofluoroalkenes. Mechanistic studies elucidated a photoredox catalyzed radical-radical coupling pathway.
View Article and Find Full Text PDFNature
November 2024
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, Hefei, China.
Polyfluoroalkyl and perfluoroalkyl substances (PFASs) are found in many everyday consumer products, often because of their high thermal and chemical stabilities, as well as their hydrophobic and oleophobic properties. However, the inert carbon-fluorine (C-F) bonds that give PFASs their properties also provide resistance to decomposition through defluorination, leading to long-term persistence in the environment, as well as in the human body, raising substantial safety and health concerns. Despite recent advances in non-incineration approaches for the destruction of functionalized PFASs, processes for the recycling of perfluorocarbons (PFCs) as well as polymeric PFASs such as polytetrafluoroethylene (PTFE) are limited to methods that use either elevated temperatures or strong reducing reagents.
View Article and Find Full Text PDFNature
November 2024
Department of Chemistry, Colorado State University, Fort Collins, Colorado, USA.
Organic halides are highly useful compounds in chemical synthesis, where the halide serves as a versatile functional group for elimination, substitution, and cross-coupling reactions with transition metals or photocatalysis. However, the activation of carbon-fluorine bonds, the most commercially abundant organohalide and found in PFAS, or "forever chemicals", are much rarer. Current approaches based on photoredox chemistry for activation of small molecule carbon-fluorine (C-F) bonds are limited by the substrates and transition-metal catalysts needed.
View Article and Find Full Text PDFMembranes (Basel)
October 2024
Institute for Nanotechnology and Water Sustainability, College of Science, Engineering and Technology, University of South Africa, Johannesburg 1709, South Africa.
Perfluoroalkyl and polyfluoroalkyl substances (PFASs) are persistent compounds characterized by stable C-F bonds giving them high thermal and chemical stability. Numerous studies have highlighted the presence of PFASs in the environment, surface waters and animals and humans. Exposure to these chemicals has been found to cause various health effects and has necessitated the need to develop methods to remove them from the environment.
View Article and Find Full Text PDFEnviron Sci Pollut Res Int
August 2024
Faculty of Chemical and Energy Engineering, Universiti Teknologi Malaysia, 81310, Skudai, Johor, Malaysia.
It is undeniable that removal efficiency is the main factor in coagulation-flocculation (C-F) process for wastewater treatment. However, as far as environmental safety is concerned, the ecotoxicological aspect of the C-F process needs to be examined further. In this study, a systematic review was performed based on publications related to the toxicity research in C-F technology for wastewater treatment.
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