Regioselective Synthesis of Benzimidazolones via Cascade C-N Coupling of Monosubstituted Ureas
Johannes B. Ernst, Nicholas E. S. Tay, Nathan T. Jui* and Stephen L. Buchwald*
*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu, njuimit.edu
J. B. Ernst, N. E. S. Tay, N. T. Jui, S. L. Buchwald, Org. Lett., 2014, 16, 3844-3845.
DOI: 10.1021/ol501531q
Abstract
In a direct method for the regioselective construction of benzimidazolones, a single palladium catalyst couples monosubstituted urea substrates with differentially substituted 1,2-dihaloaromatic systems via a cascade of two discrete and highly chemoselective C-N bond-forming processes. The method allows a predictable formation of complex heterocycles from simple, readily available starting materials.
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ID: J54-Y2014