Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective 1,2-Arylfluorination of Internal Enamides

Yang Xi; Chenchen Wang; Qian Zhang; Jingping Qu; Yifeng Chen

doi:10.1002/anie.202012882

Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective 1,2-Arylfluorination of Internal Enamides

Angew Chem Int Ed Engl. 2021 Feb 1;60(5):2699-2703. doi: 10.1002/anie.202012882. Epub 2020 Nov 26.

Authors

Yang Xi¹, Chenchen Wang¹, Qian Zhang¹, Jingping Qu¹, Yifeng Chen¹

Affiliation

¹ Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai, 200237, China.

PMID: 33052594
DOI: 10.1002/anie.202012882

Abstract

We herein describe a palladium-catalyzed three-component coupling of internal enamides, arylboronic acids, and Selectfluor to access the chiral β-fluoroaminated moiety with up to 99 % ee. The prefunctionalized oxazolidinone substituted alkene enables the expedient construction of two vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities. The synthetic application is exhibited by selective transformation of the product into various vicinal benzylic fluoride derivatives.

Keywords: arylfluorination; enamide; intermolecular reaction; palladium; vicinal stereocenters.

Abstract

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