Palladium-catalyzed asymmetric synthesis of allylic fluorides

Matthew H. Katcher; Abigail G. Doyle

doi:10.1021/ja109120n

Palladium-catalyzed asymmetric synthesis of allylic fluorides

Matthew H. Katcher, Abigail G. Doyle

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

167 Scopus citations

Abstract

The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C-F bond formation occurs by an S_N2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.

Original language	English (US)
Pages (from-to)	17402-17404
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	132
Issue number	49
DOIs	https://doi.org/10.1021/ja109120n
State	Published - Dec 15 2010

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja109120n

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abstract = "The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C-F bond formation occurs by an SN2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.",

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AU - Doyle, Abigail G.

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N2 - The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C-F bond formation occurs by an SN2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.

AB - The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C-F bond formation occurs by an SN2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.

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JO - Journal of the American Chemical Society

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Palladium-catalyzed asymmetric synthesis of allylic fluorides

Abstract

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