Yakubov, Shahboz and Barham, Joshua P. (2020) H Photosensitized direct C-H fluorination and trifluoromethylation in organic synthesis. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 16. pp. 2151-2192. ISSN 1860-5397
Full text not available from this repository. (Request a copy)Abstract
The importance of fluorinated products in pharmaceutical and medicinal chemistry has necessitated the development of synthetic fluorination methods, of which direct C-H fluorination is among the most powerful. Despite the challenges and limitations associated with the direct fluorination of unactivated C-H bonds, appreciable advancements in manipulating the selectivity and reactivity have been made, especially via transition metal catalysis and photochemistry. Where transition metal catalysis provides one strategy for C-H bond activation, transition-metal-free photochemical C-H fluorination can provide a complementary selectivity via a radical mechanism that proceeds under milder conditions than thermal radical activation methods. One exciting development in C-F bond formation is the use of small-molecule photosensitizers, allowing the reactions i) to proceed under mild conditions, ii) to be user-friendly, iii) to be cost-effective and iv) to be more amenable to scalability than typical photoredox-catalyzed methods. In this review, we highlight photosensitized C-H fluorination as a recent strategy for the direct and remote activation of C-H (especially C(sp(3))-H) bonds. To guide the readers, we present the developing mechanistic understandings of these reactions and exemplify concepts to assist the future planning of reactions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | TRIPLET-TRIPLET ABSORPTION; SELECTIVE PHOTOCHEMICAL FLUORINATION; VISIBLE-LIGHT PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; ENERGY-TRANSFER; ELECTROPHILIC FLUORINATION; EXCITED-STATE; F BOND; AROMATIC-HYDROCARBONS; RADICAL FLUORINATION; C-H activation; energy transfer; fluorination; photocatalysis; photosensitization; visible light |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Petra Gürster |
| Date Deposited: | 16 Apr 2021 05:39 |
| Last Modified: | 16 Apr 2021 05:39 |
| URI: | https://pred.uni-regensburg.de/id/eprint/43853 |
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