- Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates.
Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates.
Chemistry (Weinheim an der Bergstrasse, Germany) (2017-06-27)
Chaoren Shen, Zhihong Wei, Haijun Jiao, Xiao-Feng Wu
PMID28650074
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 BuPAd