Optimized synthesis of the trifluoromethylator, 1, 10-phenanthroline trifluoromethyl copper(I)

Copper-based trifluoromethylating agents have many pharmaceutical and industrial applications such as in the synthesis of blockbuster drugs, e.g., Celebrex. Prozac. Trifluoromethylated aromatic compounds are found as active Ingredients In a wide array of medicine. The "trifluoromethyl" group is a collection of four atoms, denoted CF₃. It is an important structural motif in a variety of useful chemical compounds, such as the pharmaceutical drugs and agrochemicals shown in Fig. 1 below.
An important example of a trifluoromethylating agent is 1, 10·phenanthroline trifluoromethylcopper(I) (phenCuCF₃), dubbed the Trifluoromethylator shown in Fig. 2. Our overarching research goal is to develop an easier method than the current published procedure for synthesizing the Trifluoromethylator as shown in Fig. 3. Particularly, the most tedious part of the original procedure was the synthesis of air-, moisture-, and temperature-sensitive copper(I) t-butoxide (CuOtBu), a hard to purify, commercially unavailable compound needed for the first step, namely the synthesis of the intermediate 1,10-phenanthroline copper(I} t-butoxide (phenCuOtBu).
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Abstract/Description: Copper-based trifluoromethylating agents have many pharmaceutical and industrial applications such as in the synthesis of blockbuster drugs, e.g., Celebrex. Prozac. Trifluoromethylated aromatic compounds are found as active Ingredients In a wide array of medicine. The "trifluoromethyl" group is a collection of four atoms, denoted CF₃. It is an important structural motif in a variety of useful chemical compounds, such as the pharmaceutical drugs and agrochemicals shown in Fig. 1 below. An important example of a trifluoromethylating agent is 1, 10·phenanthroline trifluoromethylcopper(I) (phenCuCF₃), dubbed the Trifluoromethylator shown in Fig. 2. Our overarching research goal is to develop an easier method than the current published procedure for synthesizing the Trifluoromethylator as shown in Fig. 3. Particularly, the most tedious part of the original procedure was the synthesis of air-, moisture-, and temperature-sensitive copper(I) t-butoxide (CuOtBu), a hard to purify, commercially unavailable compound needed for the first step, namely the synthesis of the intermediate 1,10-phenanthroline copper(I} t-butoxide (phenCuOtBu).
Subject(s): Undergraduate Research
Copper-based trifluoromethylating agents
Optimized synthesis