Soft Fluorination of 4-Alkylpyridines

Soft Fluorination of 4-Alkylpyridines

We report the mild and selective mono- and difluorination of 4-alkylpyridines. The process involves soft-dearomatization of pyridines to the corresponding alkylidene dihydropyridines and treatment with Selectfluor. The reaction tolerates a broad range of functional groups, including those bearing ac...

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Veröffentlicht in:Organic letters 2023-12, Vol.25 (48), p.8628-8633
Hauptverfasser: Rasheed, Faizan, Shi, Jiaqi, Zeng, Tao, Krishna, Yarkali, Fishlock, Dan, Orellana, Arturo
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container_end_page 8633
container_issue 48
container_start_page 8628
container_title Organic letters
container_volume 25
creator Rasheed, Faizan
Shi, Jiaqi
Zeng, Tao
Krishna, Yarkali
Fishlock, Dan
Orellana, Arturo
description We report the mild and selective mono- and difluorination of 4-alkylpyridines. The process involves soft-dearomatization of pyridines to the corresponding alkylidene dihydropyridines and treatment with Selectfluor. The reaction tolerates a broad range of functional groups, including those bearing acidic and weak C-H bonds. In addition, selective fluorination of 4-alkylpyridines attached to 2-alkylpyridines and 2-alkylpyrimidines can be achieved in good yields, but a 4-alkylpyridine tethered to a 4-alkylpyrimidine is fluorinated at both heterobenzylic positions.
doi_str_mv 10.1021/acs.orglett.3c03482
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title Soft Fluorination of 4-Alkylpyridines
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