Direct C-H bond (Hetero)arylation of thiazole derivatives at 5-position catalyzed by N-heterocyclic carbene palladium complexes at low catalyst loadings under aerobic conditions

Publication date: Available online 17 June 2019Source: Journal of Organometallic ChemistryAuthor(s): Bei-Bei Ma, Xiao-Bing Lan, Dong-Sheng Shen, Feng-Shou Liu, Chang XuAbstractA highly efficient and practical protocol has been developed for the synthesis of 5-(hetero)arylated thiazole derivatives via an N-heterocyclic carbene palladium (Pd-NHC) complex catalyzed direct C-H arylation reaction. Utilization of this methodology, the arylation of substituted thiazoles with (hetero)aryl bromides efficiently proceeded at low catalyst loading (0.1–0.05 mol%) and under aerobic conditions. A variety of (hetero)aryl bromides, even some strongly deactivated or highly congested (hetero)aryl bromides, with a broad range of functional groups were compatible under the optimal reaction conditions. In all cases, the target products were afforded in moderate to quantitative yields.Graphical abstract

Source: Journal of Organometallic Chemistry - June 18, 2019 Category: Chemistry Source Type: research