Iridium-Catalyzed ortho-Selective C–H Silylation of Aromatic Compounds Directed toward the Synthesis of π-Conjugated Molecules with Lewis Acid–Base Interaction

2015 ◽  
Vol 17 (7) ◽  
pp. 1758-1761 ◽  
Author(s):  
Takayuki Wakaki ◽  
Motomu Kanai ◽  
Yoichiro Kuninobu
Synlett ◽  
2018 ◽  
Vol 29 (16) ◽  
pp. 2093-2107 ◽  
Author(s):  
Yoichiro Kuninobu

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 Introduction2 Regioselective C–H Transformations Controlled by Noncovalent Bond Interactions2.1 Regioselective C–H Transformations Controlled by Lewis Acid–Base Interaction between Two Substrates2.2 Regioselective C–H Transformation Controlled by Hydrogen Bonding between Ligand and Substrate2.3 Regioselective C–H Transformations Controlled by Lewis Acid–Base Interactions between Ligands and Substrates3 Trifluoromethylation and Related Transformations of Six-Membered Heteroaromatic Compounds3.1 2-Position-Selective C–H Trifluoromethylation of Six-Membered Heteroaromatic Compounds3.2 4-Position-Selective C–H Trifluoromethylation of Six-Membered Heteroaromatic Compounds3.3 Benzyl Position-Selective C–H Trifluoromethylation of Six-Membered Heteroaromatic Compounds4 C–H Transformations Leading to the Synthesis of Organic Functional Materials4.1 Heteroatom-Containing π-Conjugated Molecules4.2 π-Conjugated Molecules Containing a Lewis Acid–Base Interaction4.3 Soluble Polyimide Derivatives5 Conclusions


2019 ◽  
Vol 43 (34) ◽  
pp. 13630-13634 ◽  
Author(s):  
Guohong Wang ◽  
Min Li ◽  
Wenmin Pang ◽  
Min Chen ◽  
Chen Tan

The Lewis acid-base interaction between B(iii) Lewis acids and the pyridazine moiety reduced the electron density from the Ni center and in situ modulated the pyridazine-imine nickel catalyzed ethylene (co)polymerisation.


RSC Advances ◽  
2020 ◽  
Vol 10 (15) ◽  
pp. 8780-8789 ◽  
Author(s):  
Prerna Joshi ◽  
Raman Vedarajan ◽  
Anjaiah Sheelam ◽  
Kothandaraman Ramanujam ◽  
Bernard Malaman ◽  
...  

A non-polymer crystalline organoboron electrolyte results in the formation of nano-channels for directional conduction of Li ions, owing to presence of boron, allowing Lewis acid–base interaction.


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