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Regioselective Transition-Metal-Catalyzed C–H Functionalization of Anilines
Anilines are a vital synthetic core of pharmaceuticals, agrochemicals, natural products and building blocks. Metal-catalyzed C–H functionalization has emerged as a powerful tool to derivatize biologically relevant molecules....
Regioselective Transition-Metal-Catalyzed C–H Functionalization of Anilines
Anilines are a vital synthetic core of pharmaceuticals, agrochemicals, natural products and building blocks. Metal-catalyzed C–H functionalization has emerged as a powerful tool to derivatize biologically relevant molecules....
Beyond C2 and C3
The indole scaffold will continue to play a vital part in the future of drug discovery and agrochemical development. Because of this, the necessity for elegant techniques to enable selective C–H functionalization is vast. Early...
Beyond C2 and C3
The indole scaffold will continue to play a vital part in the future of drug discovery and agrochemical development. Because of this, the necessity for elegant techniques to enable selective C–H functionalization is vast. Early...
Ruthenium(II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group
Jamie A. Leitch, Philippe B. Wilson, Claire L. McMullin, Mary F. Mahon, Yunas Bhonoah, Ian H. Williams, Christopher G. Frost
Jul 27, 2016
Herein, we report the ruthenium-catalyzed ortho C–H alkenylation of a wide range of N-aryloxazolidinone scaffolds. Alkenylation was achieved with complete monoselectivity with a scope of 27 examples in 2-MeTHF. Yields ranged...
Ruthenium(II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group
Jamie A. Leitch, Philippe B. Wilson, Claire L. McMullin, Mary F. Mahon, Yunas Bhonoah, Ian H. Williams, Christopher G. Frost
Jul 27, 2016
Herein, we report the ruthenium-catalyzed ortho C–H alkenylation of a wide range of N-aryloxazolidinone scaffolds. Alkenylation was achieved with complete monoselectivity with a scope of 27 examples in 2-MeTHF. Yields ranged...
Ruthenium-Catalyzed para-Selective C−H Alkylation of Aniline Derivatives
Jamie A. Leitch, Claire L. McMullin, Andrew J. Paterson, Mary F. Mahon, Yunas Bhonoah, Christopher G. Frost
Nov 20, 2017
The para-selective C−H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N−H-activated cyclometalate formed in situ. Experimental and DFT...
Ruthenium-Catalyzed para-Selective C−H Alkylation of Aniline Derivatives
Jamie A. Leitch, Claire L. McMullin, Andrew J. Paterson, Mary F. Mahon, Yunas Bhonoah, Christopher G. Frost
Nov 20, 2017
The para-selective C−H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N−H-activated cyclometalate formed in situ. Experimental and DFT...
Catalytic meta-selective C–H functionalization to construct quaternary carbon centres
A catalytic meta-selective C–H functionalization of 2-phenylpyridines using a range of tertiary halides is described. The protocol is simple to perform and uses commercially available reagents to construct challenging quaternary...
Ruthenium catalyzed remote C4-selective C–H functionalisation of carbazoles via σ-activation
Jamie A. Leitch, Callum J. Heron, Janette Mcknight, Gabriele Kociok-Köhn, Yunas Bhonoah, Christopher G. Frost
Dec 18, 2017
We report the C4-selective C–H alkylation of carbazole derivatives furnished with a pyrimidine directing group at N9. This was realized using ruthenium catalyzed r-activation methodology, whereby C–H activation at C1 enables the...
Catalytic meta-selective C–H functionalization to construct quaternary carbon centres
A catalytic meta-selective C–H functionalization of 2-phenylpyridines using a range of tertiary halides is described. The protocol is simple to perform and uses commercially available reagents to construct challenging quaternary...
Modes of activation of organometallic iridium complexes for catalytic water and C–H oxidation
Andrew J. Ingram, Arron B. Wolk, Cornelia Flender, Jialing Zhang, Christopher J. Johnson, Ulrich Hintermair, Robert H. Crabtree, Mark A. Johnson, Richard N. Zare
Jan 06, 2014
Sodium periodate (NaIO4) is added to Cp*IrIII (Cp* = C5Me5–) or (cod)IrI (cod = cyclooctadiene) complexes, which are water and C–H oxidation catalyst precursors, and the resulting aqueous reaction is investigated from...
Ruthenium catalyzed remote C4-selective C–H functionalisation of carbazoles via σ-activation
Jamie A. Leitch, Callum J. Heron, Janette Mcknight, Gabriele Kociok-Köhn, Yunas Bhonoah, Christopher G. Frost
Dec 18, 2017
We report the C4-selective C–H alkylation of carbazole derivatives furnished with a pyrimidine directing group at N9. This was realized using ruthenium catalyzed r-activation methodology, whereby C–H activation at C1 enables the...
Modes of activation of organometallic iridium complexes for catalytic water and C–H oxidation
Andrew J. Ingram, Arron B. Wolk, Cornelia Flender, Jialing Zhang, Christopher J. Johnson, Ulrich Hintermair, Robert H. Crabtree, Mark A. Johnson, Richard N. Zare
Jan 06, 2014
Sodium periodate (NaIO4) is added to Cp*IrIII (Cp* = C5Me5–) or (cod)IrI (cod = cyclooctadiene) complexes, which are water and C–H oxidation catalyst precursors, and the resulting aqueous reaction is investigated from...
Remote C6-Selective Ruthenium-Catalyzed C-H Alkylation of Indole Derivatives via σ-Activation
Jamie A. Leitch, Claire L. McMullin, Mary F. Mahon, Yunas Bhonoah, Christopher G. Frost
Apr 07, 2017
The site-selective functionalization of an indole template offers exciting possibilities for the derivatization of molecules with useful biological properties. Herein, we report the remote C6-selective C-H alkylation of...
Electrostatically-directed Pd-catalysis in combination with C-H activation
Systems incorporating catalyst-substrate non-covalent interactions are emerging as a versatile approach to address site-selectivity challenges in remote functionalization reactions. Given the achievements that have been made in...
Catalytic C(sp3)-H bond activation in tertiary alkylamines.
Jesus Rodrigalvarez, Manuel Nappi, Hiroki Azuma, Nils J Flodén, Matthew E Burns, Matthew J Gaunt
Feb 03, 2021
The development of robust catalytic methods to assemble tertiary alkylamines provides a continual challenge to chemical synthesis. In this regard, transformation of a traditionally unreactive C-H bond, proximal to the nitrogen...
Electrostatically-directed Pd-catalysis in combination with C-H activation
Systems incorporating catalyst-substrate non-covalent interactions are emerging as a versatile approach to address site-selectivity challenges in remote functionalization reactions. Given the achievements that have been made in...
Published by: Chemical science
Selective Reductive Elimination at Alkyl Palladium(IV) by Dissociative Ligand Ionization
A palladium(II)-catalyzed γ-C-H amination of cyclic alkyl amines to deliver highly substituted azetidines is reported. The use of a benziodoxole tosylate oxidant in combination with AgOAc was found to be crucial for controlling...
Remote C6-Selective Ruthenium-Catalyzed C-H Alkylation of Indole Derivatives via σ-Activation
Jamie A. Leitch, Claire L. McMullin, Mary F. Mahon, Yunas Bhonoah, Christopher G. Frost
Apr 07, 2017
The site-selective functionalization of an indole template offers exciting possibilities for the derivatization of molecules with useful biological properties. Herein, we report the remote C6-selective C-H alkylation of...
Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation.
The enantioselective amination of C(sp3)-H bonds is a powerful synthetic transformation yet highly challenging to achieve in an intermolecular sense. We have developed a family of anionic variants of the...
Published by: Journal of the American Chemical Society
The ortho effect in directed C-H activation.
Balázs L Tóth, Anna Monory, Orsolya Egyed, Attila Domján, Attila Bényei, Bálint Szathury, Zoltán Novák, András Stirling
Jul 28, 2021
The success of transition metal-catalysed ortho-directed C-H activation is often plagued by the effects of undesirable interactions between the directing group (DG) and other groups introduced into the aromatic core of the...
Bridging Plastic Recycling and Organic Catalysis
Tengfei Li, Arjun Vijeta, Carla Casadevall, Alexander S Gentleman, Tijmen Euser, Erwin Reisner
Aug 25, 2022
Chemical recycling of synthetic polymers represents a promising strategy to deconstruct plastic waste and make valuable products. Inspired by small-molecule C-H bond activation, a visible-light-driven reaction is developed to...
Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles.
The development of new chemical transformations based on catalytic functionalization of unactivated C-H bonds has the potential to simplify the synthesis of complex molecules dramatically. Transition metal catalysis has emerged...
Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation
Catherine L. Lyall, Camilla C. Shotton, Monserrat Pérez-salvia, Dan Pantos, Simon E. Lewis
Nov 18, 2014
We report the first boron-substituted naphthalenediimides (NDIs), prepared by iridium catalysed C–H activation. When the NDI substrates bear N-benzyl substituents, the naphthyl NDI core is borylated in preference, suggestive of...
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