Abstract
A highly selective copper-catalyzed trifluoromethylation of indoles is reported with the assistance of a removable directing group. This protocol provides an easy and rapid method to various 2-position-selective trifluoromethylated heteroarenes including indoles, pyrroles, benzofuran, and acetanilide. What is more, the reaction takes place at ambient conditions without any external ligand or additive.
Highlights
The introduction of trifluoromethyl (CF3) groups into heteroarenes enjoys a privileged role in medicinal chemistry, since it can substantially alter their properties, such as metabolic stability, lipophilicity and ability to penetrate the blood-brain barrier (Shimizu and Hiyama, 2005; Schlosser, 2006; Hagmann, 2008; Boechat and Bastos, 2010; Nie et al, 2011; Wang et al, 2014; Gouverneur and Seppelt, 2015)
Indoles represent ubiquitous structural motifs found in biologically active natural products and pharmaceutical compounds (Lee et al, 2015; Chripkova et al, 2016; Sravanthi and Manju, 2016; Goyal et al, 2018; Kaur et al, 2019)
Direct trifluoromethylation of indoles offers an attractive alternative to the workers in the field of medicinal chemistry and biochemistry
Summary
The introduction of trifluoromethyl (CF3) groups into heteroarenes enjoys a privileged role in medicinal chemistry, since it can substantially alter their properties, such as metabolic stability, lipophilicity and ability to penetrate the blood-brain barrier (Shimizu and Hiyama, 2005; Schlosser, 2006; Hagmann, 2008; Boechat and Bastos, 2010; Nie et al, 2011; Wang et al, 2014; Gouverneur and Seppelt, 2015). It has a great potential in the development of new pharmaceutical chemicals (Scheme 1). The key to our success is the installation of a suitable Boc director on the indole nitrogen atom
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