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
Hauptverfasser: Zong, Yuwei, Tang, Yihan, Tsui, Gavin Chit
Format: Artikel
Sprache:eng
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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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02294