Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 16, Issue -, Pages 2151-2192Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.16.183
Keywords
C-H activation; energy transfer; fluorination; photocatalysis; photosensitization; visible light
Categories
Funding
- DAAD Scholarship
- University of Regensburg
- SynCat programme of the Elite Network of Bavaria
- Alexander von Humboldt Foundation
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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.
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