Chemical libraries via sequential C-H functionalization of phenols.
Phenols provide a useful template for diversification via sequential hydroarylation reactions. Specifically, a protocol has been developed that begins with the hydroarylation of cinnamic acids by 3,5-dimethoxyphenol to produce dihydrocoumarins. This activated ester undergoes facile ring-opening with amines to form a C-N bond and regenerate a phenol. The resulting phenol can be further functionalized via a second hydroarylation reaction. Thus, in 3-4 steps, a phenol is coupled with a cinnamic acid, an amine, and a cinnamic or propiolic acid.
Li
Kelin
K
Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, 2010 Malott Hall, Lawrence, Kansas 66045-7582, USA.
Tunge
Jon A
JA
D002244:Carbon / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*
D010636:Phenols; D002244:Carbon; D006859:Hydrogen