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Updated: Feb 27, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates
Chaoren Shen1, Zhihong Wei1, Haijun Jiao1
1Leibniz-Institut für Katalyse e.V., Universität Rostock, Albert-Einstein-Strasse 29a, 18059, Rostock, Germany.
Abstract:
The palladium-catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C-Br bond versus C-OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) vs. 1,1'-bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd2 and tBu3 P prefer the selective C-Br bond activation and are solvent insensitive.
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