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Synthesis of Highly Functionalizable Symmetrically and Unsymmetrically Substituted Triarylboranes from Bench‐Stable Boron Precursors

Matthias Ferger, Sarina M. Berger, Florian Rauch, Markus Schönitz, Jessica Rühe, Johannes Krebs, Alexandra Friedrich, Todd B. Marder

2021Chemistry - A European Journal19 citationsDOIOpen Access PDF

Abstract

Abstract A novel and convenient methodology for the one‐pot synthesis of sterically congested triarylboranes by using bench‐stable aryltrifluoroborates as the boron source is reported. This procedure gives systematic access to symmetrically and unsymmetrically substituted triarylboranes of the types BAr 2 Ar’ and BArAr'Ar’’, respectively. Three unsymmetrically substituted triarylboranes as well as their iridium‐catalyzed C−H borylation products are reported. These borylated triarylboranes contain one to three positions that can subsequently be orthogonally functionalized in follow‐up reactions, such as Suzuki‐Miyaura cross‐couplings or Sonogashira couplings.

Topics & Concepts

BorylationSonogashira couplingIridiumBoronChemistryCombinatorial chemistrySteric effectsCatalysisPolymer chemistryOrganic chemistryPalladiumArylAlkylOrganoboron and organosilicon chemistryBoron Compounds in ChemistryCatalytic Cross-Coupling Reactions
Synthesis of Highly Functionalizable Symmetrically and Unsymmetrically Substituted Triarylboranes from Bench‐Stable Boron Precursors | Litcius