Benzotrifluoride and Derivatives: Useful Solvents for Organic Synthesis and Fluorous Synthesis

Abstract

Benzotrifluoride (BTF, trifluoromethylbenzene, alpha,alpha,alpha-trifluorotoluene, C6H5CF3) and related compounds are introduced as new solvents for traditional organic synthesis and for fluorous synthesis. BTF is more environmentally friendly than many other organic solvents and is available in large quantities. BTF is relatively inert and is suitable for use as a solvent for a wide range of chemistry including ionic, transition-metal catalyzed and thermal reactions. It is especially useful for radical reactions, where it may replace benzene as the current solvent of choice for many common transformations. BTF and related solvents are also crucial components of fluorous synthesis since they can dissolve both standard organic molecules and highly fluorinated molecules. This chapter provides an overview of the reactivity and toxicological properties of BTF and analogs and then summarizes their recent uses as reaction solvents in both traditional organic and new fluorous synthesis.