Transformation of Anionically Activated Trifluoromethyl Groups to Heterocycles under Mild Aqueous Conditions
journal contributionposted on 2011-04-01, 00:00 authored by Jennifer X. Qiao, Tammy C. Wang, Carol Hu, Jianqing Li, Ruth R. Wexler, Patrick Y. S. Lam
The (hetero)aromatic trifluoromethyl group is present in many biologically active molecules and is generally considered to be chemically stable. In this paper, a convenient one-step synthesis of C−C linked aryl−heterocycles or heteroaryl−heterocycles in good to excellent yields via the reaction of anionically activated trifluoromethyl groups with amino nucleophiles containing a second NH, OH, or SH nucleophile in 1 N sodium hydroxide is reported. The method has high functional group tolerability and is potentially useful in parallel synthesis.