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Interrogating Pd(II) anion metathesis using a bifunctional chemical probe: a transmetalation switch

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Author(s)

John J Molloy, Ciaran P. Seath, Matthew J West, Calum McLaughlin, Neal J. Fazakerley, Alan R. Kennedy, David James Nelson, Allan J. B. Watson

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Abstract

Ligand metathesis of Pd(II) complexes is mechanistically essential for cross-coupling. We present a study of halide→OH anion metathesis of (Ar)PdII complexes using vinylBPin as a bifunctional chemical probe with Pd(II)-dependent cross-coupling pathways. We identify the variables that profoundly impact this event and allow control to be leveraged. This then allows control of cross-coupling pathways via promotion or inhibition of organoboron transmetalation, leading to either Suzuki-Miyaura or Mizoroki-Heck products. We show how this transmetalation switch can be used to synthetic gain in a cascade cross-coupling/Diels-Alder reaction, delivering borylated or non-borylated carbocycles, including steroid-like scaffolds.
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Original languageEnglish
Pages (from-to)126-130
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number1
Early online date19 Dec 2017
DOIs
Publication statusPublished - 10 Jan 2018

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