» Articles » PMID: 28345205

Para-Selective C-H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis

Overview
Specialty Chemistry
Date 2017 Mar 28
PMID 28345205
Citations 32
Authors
Affiliations
Soon will be listed here.
Abstract

para-Selective C-H borylation of benzamides and pyridines has been achieved by cooperative iridium/aluminum catalysis. A combination of iridium catalysts commonly employed for arene C-H borylation and bulky aluminum-based Lewis acid catalysts provides an unprecedented strategy for controlling the regioselectivity of C-H borylation to give variously substituted (hetero)arylboronates, which are versatile synthetic intermediates for complex multi-substituted aromatic compounds.

Citing Articles

Repurposing a supramolecular iridium catalyst secondary Zn⋯O[double bond, length as m-dash]C weak interactions between the ligand and substrate leads to -selective C(sp)-H borylation of benzamides with unusual kinetics.

Trouve J, Delahaye V, Tomasini M, Rajeshwaran P, Roisnel T, Poater A Chem Sci. 2024; 15(30):11794-11806.

PMID: 39092112 PMC: 11290415. DOI: 10.1039/d4sc01515k.


Trialkoxysilane-Induced Iridium-Catalyzed para-Selective C-H Bond Borylation of Arenes.

Ju G, Huang Z, Zhao Y Nat Commun. 2024; 15(1):2847.

PMID: 38565860 PMC: 10987550. DOI: 10.1038/s41467-024-47205-8.


Applications of Transition Metal-Catalyzed -Fluorine-Directed C-H Functionalization of (Poly)fluoroarenes in Organic Synthesis.

Budiman Y, Perutz R, Steel P, Radius U, Marder T Chem Rev. 2024; 124(8):4822-4862.

PMID: 38564710 PMC: 11046440. DOI: 10.1021/acs.chemrev.3c00793.


Cooperative activation of carbon-hydrogen bonds by heterobimetallic systems.

Lachguar A, Pichugov A, Neumann T, Dubrawski Z, Camp C Dalton Trans. 2023; 53(4):1393-1409.

PMID: 38126396 PMC: 10804807. DOI: 10.1039/d3dt03571a.


Kinetic and thermodynamic control of C(sp)-H activation enables site-selective borylation.

Roque J, Shimozono A, Pabst T, Hierlmeier G, Peterson P, Chirik P Science. 2023; 382(6675):1165-1170.

PMID: 38060669 PMC: 10898344. DOI: 10.1126/science.adj6527.