Abstract
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 π-conjugated molecules containing either heteroatom(s) or a Lewis acid–base interaction.
1 Introduction
2 Regioselective C–H Transformations Controlled by Noncovalent Bond Interactions
2.1 Regioselective C–H Transformations Controlled by Lewis Acid–Base Interaction between Two Substrates
2.2 Regioselective C–H Transformation Controlled by Hydrogen Bonding between Ligand and Substrate
2.3 Regioselective C–H Transformations Controlled by Lewis Acid–Base Interactions between Ligands and Substrates
3 Trifluoromethylation and Related Transformations of Six-Membered Heteroaromatic Compounds
3.1 2-Position-Selective C–H Trifluoromethylation of Six-Membered Heteroaromatic Compounds
3.2 4-Position-Selective C–H Trifluoromethylation of Six-Membered Heteroaromatic Compounds
3.3 Benzyl Position-Selective C–H Trifluoromethylation of Six-Membered Heteroaromatic Compounds
4 C–H Transformations Leading to the Synthesis of Organic Functional Materials
4.1 Heteroatom-Containing π-Conjugated Molecules
4.2 π-Conjugated Molecules Containing a Lewis Acid–Base Interaction
4.3 Soluble Polyimide Derivatives
5 Conclusions
Key words C–H transformations - regioselectivity - noncovalent interactions - hydrogen bonding - borylation - silylation
