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. 2012 Aug 17;14(16):4094-7.
doi: 10.1021/ol301739f. Epub 2012 Jul 30.

Pd-catalyzed C-H fluorination with nucleophilic fluoride

Kate B McMurtrey  1 , Joy M Racowski, Melanie S Sanford
Affiliations

Pd-catalyzed C-H fluorination with nucleophilic fluoride

Kate B McMurtrey et al. Org Lett. .

Abstract

The palladium-catalyzed C-H fluorination of 8-methylquinoline derivatives with nucleophilic fluoride is reported. This transformation involves the use of AgF as the fluoride source in combination with a hypervalent iodine oxidant. Both the scope and mechanism of the reaction are discussed.

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Figures

Figure 1
Figure 1
Prices for commercial fluorine sources (based on largest quantity commercially available from Sigma Aldrich in >95% purity)
Scheme 1
Scheme 1
Pd-Catalyzed C–H Fluorination with F+ Reagents
Scheme 2
Scheme 2
Proposed Sequence
Scheme 3
Scheme 3
Two possible routes to B from A, AgF and ArI(OPiv)2
See this image and copyright information in PMC

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