Development of Novel C-H Bond Transformations and Their Application to the Synthesis of Organic Functional Molecules

This personal account summarizes our recent progress in the development of C-H transformations. We achieved ortho-selective C-H borylations and silylations by using Lewis acid-base interaction between two substrates and we achieved meta-and ortho-selective C-H borylations by using hydrogen bonding or Lewis acid-base interaction between a hydrogen donor or Lewis acid unit of a ligand and a functional group of a substrate. Regioselective C-H trifluoromethylations and related reactions of six-membered heteroaromatic compounds were realized at their 2- and 4-positions and at their benzylic positions. In addition, we developed C-H transformations directed towards the synthesis of organic functional materials, such as highly soluble polyimides or -conjugated molecules containing either heteroatom(s) or a Lewis acid-base interaction. 1Introduction 2Regioselective C-H Transformations Controlled by Noncovalent Bond Interactions 2.1Regioselective C-H Transformations Controlled by Lewis Acid-Base Interaction between Two Substrates 2.2Regioselective C-H Transformation Controlled by Hydrogen Bonding between Ligand and Substrate 2.3Regioselective C-H Transformations Controlled by Lewis Acid-Base Interactions between Ligands and Substrates 3Trifluoromethylation and Related Transformations of Six-Membered Heteroaromatic Compounds 3.12-Position-Selective C-H Trifluoromethylation of Six-Membered Heteroaromatic Compounds 3.24-Position-Selective C-H Trifluoromethylation of Six-Membered Heteroaromatic Compounds 3.3Benzyl Position-Selective C-H Trifluoromethylation of Six-Membered Heteroaromatic Compounds 4C-H Transformations Leading to the Synthesis of Organic Functional Materials 4.1Heteroatom-Containing -Conjugated Molecules 4.2-Conjugated Molecules Containing a Lewis Acid-Base Interaction 4.3Soluble Polyimide Derivatives 5Conclusions