Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates

Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates
Chaoren Shen, Xiao-Feng Wu, Haijun Jiao, Zhihong Wei
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 tBu3P prefer the selective C−Br bond activation and are solvent insensitive. Keep control: Palladium-catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The influencing effects of different solvents (polar vs. non-polar) and ligands (e.g., monodentate vs. bidentate) on the chemoselectivety is discussed based on experimental observations as well as DFT calculations (see scheme; Xantphos=4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, DPPF=1,1′-bis(diphenylphosphino)ferrocene).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702015

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