Organic Letters
Organic Letters
5 years ago

Chemoselective Copper-Catalyzed Ullmann-Type Coupling of Oxazolidinones with Bromoiodoarenes

Chemoselective Copper-Catalyzed Ullmann-Type Coupling of Oxazolidinones with Bromoiodoarenes
Chong Han, Francis Gosselin, Sean M. Kelly, Laura Tung
We describe the highly selective copper-catalyzed Ullmann-type coupling of bromoiodoarenes with oxazolidinones. 3,4,7,8-Tetramethyl-1,10-phenanthroline (Me4Phen) was identified as an optimal ligand promoting the desired C–N bond formation, while minimizing the competitive bromo–iodo exchange pathway that leads to formation of iodo-substituted and bis-coupled side products. The developed method is highly selective with a >98:2 ratio of the bromo- vs iodo-substituted compounds obtained in the isolated products.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01304

DOI: 10.1021/acs.orglett.7b01304

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