Rhodium(I)-Catalyzed Defluorinative Coupling of Boronic Acids with Monofluoroalkenes
We herein describe a highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-β-monofluoroacrylates. In contrast to previous methods, the trisubstituted (Z)-alkene products were obtained in excellent dr with an inversion of double bond geometry. Experimental and computatio...
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Veröffentlicht in: | Organic letters 2022-09, Vol.24 (35), p.6380-6385 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | We herein describe a highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-β-monofluoroacrylates. In contrast to previous methods, the trisubstituted (Z)-alkene products were obtained in excellent dr with an inversion of double bond geometry. Experimental and computational studies established that Rh(I)-facilitated β-F elimination is favored over competing β-H elimination and protodemetalation. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.2c02294 |