Iridium-Catalyzed Allylic Fluorination of Trichloroacetimidates

A rapid allylic fluorination method utilizing trichloroacetimidates in conjunction with an iridium catalyst has been developed. The reaction is conducted at room temperature under ambient air and relies on Et3N·3HF reagent to provide branched allylic fluorides with complete regioselectivity. This hi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-12, Vol.133 (48), p.19318-19321
Main Authors: Topczewski, Joseph J, Tewson, Timothy J, Nguyen, Hien M
Format: Article
Language:English
Subjects:
Acetamides
Allyl Compounds - chemistry
Catalysis
Chloroacetates
Halogenation
Iridium - chemistry
Stereoisomerism
Trichloroacetic Acid - chemistry
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Summary:A rapid allylic fluorination method utilizing trichloroacetimidates in conjunction with an iridium catalyst has been developed. The reaction is conducted at room temperature under ambient air and relies on Et3N·3HF reagent to provide branched allylic fluorides with complete regioselectivity. This high-yielding reaction can be conducted on a multigram scale and shows considerable functional group tolerance. The use of [18F]KF·Kryptofix allowed 18F– incorporation in 10 min.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja2087213