Organic Chemistry Portal

Abstracts

Search:

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.

see article for more examples



Key Words

benzimidazolones


ID: J54-Y2014