Iridium-catalyzed allylic fluorination of trichloroacetimidates

Joseph J. Topczewski; Timothy J. Tewson; Hien M. Nguyen

doi:10.1021/ja2087213

Iridium-catalyzed allylic fluorination of trichloroacetimidates

Joseph J. Topczewski, Timothy J. Tewson, Hien M. Nguyen

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

109 Scopus citations

Abstract

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 Et ₃N•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.

Original language	English (US)
Pages (from-to)	19318-19321
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	48
DOIs	https://doi.org/10.1021/ja2087213
State	Published - Dec 7 2011

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abstract = "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 Et 3N•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.",

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AU - Tewson, Timothy J.

AU - Nguyen, Hien M.

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N2 - 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 Et 3N•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.

AB - 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 Et 3N•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.

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Iridium-catalyzed allylic fluorination of trichloroacetimidates

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