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

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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.

Original languageEnglish
Pages (from-to)2093-2107
Number of pages15
JournalSynlett
Volume29
Issue number16
DOIs
Publication statusPublished - Jan 1 2018

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Lewis Acids
Molecules
Substrates
Functional materials
Ligands
Polyimides
Hydrogen bonds
Functional groups
Hydrogen
Derivatives

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Development of Novel C-H Bond Transformations and Their Application to the Synthesis of Organic Functional Molecules. / Kuninobu, Yoichiro.

In: Synlett, Vol. 29, No. 16, 01.01.2018, p. 2093-2107.

Research output: Contribution to journalArticle

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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.",
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