期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 42, 页码 14824-14848出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814457
关键词
C-H activation; fluorination; radical chemistry; radiochemistry; transition-metal catalysis
资金
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
- AstraZeneca
- Diamond Light Source
- Defence Science and Technology Laboratory
- Evotec
- GlaxoSmithKline
- Janssen
- Novartis
- Pfizer
- Syngenta
- Takeda UCB
- Vertex
- Oxford-Radcliffe scholarship
- EPSRC [1923180] Funding Source: UKRI
This Review summarizes advances in fluorination by C(sp(2))-H and C(sp(3))-H activation. Transition-metal-catalyzed approaches championed by palladium have allowed the installation of a fluorine substituent at C(sp(2)) and C(sp(3)) sites, exploiting the reactivity of high-oxidation-state transition-metal fluoride complexes combined with the use of directing groups (some transient) to control site and stereoselectivity. The large majority of known methods employ electrophilic fluorination reagents, but methods combining a nucleophilic fluoride source with an oxidant have appeared. External ligands have proven to be effective for C(sp(3))-H fluorination directed by weakly coordinating auxiliaries, thereby enabling control over reactivity. Methods relying on the formation of radical intermediates are complementary to transition-metal-catalyzed processes as they allow for undirected C(sp(3))-H fluorination. To date, radical C-H fluorinations mainly employ electrophilic N-F fluorination reagents but a unique Mn-III-catalyzed oxidative C-H fluorination using fluoride has been developed. Overall, the field of late-stage nucleophilic C-H fluorination has progressed much more slowly, a state of play explaining why C-H F-18-fluorination is still in its infancy.
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