One‐Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes

Li, Zhou; Gevorgyan, Vladimir

doi:10.1002/ange.201106969

Angewandte Chemie

2011

DOI: 10.1002/ange.201106969

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One‐Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes

Zhou Li

Vladimir Gevorgyan

Abstract: Im Eintopfverfahren gelingt die Synthese von Perfluoraryloxiranen 2 durch die arylierende Epoxidierung enolisierbarer Ketone 1 mit Brompentafluorbenzol (PFPBr) und dessen Derivaten (3). PFPBr dient in dieser hoch effizienten diastereoselektiven Epoxidierung als Äquivalent für Br+ und PFP−. Die Reaktion ergibt nützliche Polyfluoraryloxirane und kann leicht im größeren Maßstab ausgeführt werden.

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Cited by 5 publications

References 33 publications

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Strain‐Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ‐Bond Nucleopalladation

Wölfl

Winter

et al. 2023

Angewandte Chemie

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The development of preparative methods for the synthesis of four-membered carbocycles is gaining increasing importance due to the widespread utility of cyclic compounds in medicinal chemistry. Herein, we report the development of a new methodology for the production of spirocyclic epoxides and aziridines containing a cyclobutane motif. In a two-step one-pot process, a bicyclo[1.1.0]butyl sulfoxide is lithiated and added to a ketone, aldehyde or imine, and the resulting intermediate is cross-coupled with an aryl triflate through CÀ C σ-bond alkoxy-or aminopalladation with concomitant epoxide or aziridine formation. After careful optimization, a remarkably efficient reaction was conceived that tolerated a broad variety of both aromatic and aliphatic substrates. Lastly, through several high yielding ring-opening reactions, we demonstrated the excellent applicability of the products as modular building blocks for the introduction of threedimensional structures into target molecules.

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Strain‐Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ‐Bond Nucleopalladation

Wölfl

Winter

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Strain‐Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ‐Bond Nucleopalladation

Wölfl

Winter

et al. 2023

Angew Chem Int Ed

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Copper‐Catalyzed Trifluoromethylation of Internal Olefinic CH Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N‐Heterocycles

Mao

Huang

et al. 2014

Chemistry A European J

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The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient CuII-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)2 as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluoromethylation. Cyclic and acyclic dithioalkyl α-oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic C-H bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF3 olefins led to multifunctionalized tetrasubstituted CF3 olefins and trifluoromethylated N-heterocycles.

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One‐Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes

Cited by 5 publications

References 33 publications

Strain‐Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ‐Bond Nucleopalladation

Strain‐Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ‐Bond Nucleopalladation

Strain‐Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ‐Bond Nucleopalladation

Copper‐Catalyzed Trifluoromethylation of Internal Olefinic CH Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N‐Heterocycles

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