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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....
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
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...
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...
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...
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...
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...
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...
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...
Revealing the Drag Instability in One-fluid Nonideal Magnetohydrodynamic Simulations of a 1D Isothermal C-shock
Abstract
C-type shocks are believed to be ubiquitous in turbulent molecular clouds thanks to ambipolar diffusion. We investigate whether the drag instability in 1D isothermal...
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...
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...
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...
Investigations into the reactivity of lithium indenyl with alpha diimines with chlorinated backbones and formation of related functional ligands and metal complexes
Chi Tien Chen, Mark E. Fischer, Caroline Windsor, Ino C. Vei, David G. Calatayud, Malcolm L H Green, Sofia I. Pascu
Nov 24, 2016
Reaction between lithium indenyl and a chlorine substituted alpha diimine of the form [{Cl(NPh)2}C)]2 unexpectedly yielded the corresponding NH rearranged derivative...
Catalysis Diimine complexes Flat aromatic organic compounds Heterobimetallic complexes Transition metal chemistry /dk/atira/pure/subjectarea/asjc/1600/1606 name=Physical and Theoretical Chemistry /dk/atira/pure/subjectarea/asjc/1600/1604 name=Inorganic Chemistry /dk/atira/pure/subjectarea/asjc/2500/2505 name=Materials Chemistry
Investigations into the reactivity of lithium indenyl with alpha diimines with chlorinated backbones and formation of related functional ligands and metal complexes
Chi Tien Chen, Mark E. Fischer, Caroline Windsor, Ino C. Vei, David G. Calatayud, Malcolm L H Green, Sofia I. Pascu
Nov 24, 2016
Reaction between lithium indenyl and a chlorine substituted alpha diimine of the form [{Cl(NPh)2}C)]2 unexpectedly yielded the corresponding NH rearranged derivative...
Catalysis Diimine complexes Flat aromatic organic compounds Heterobimetallic complexes Transition metal chemistry /dk/atira/pure/subjectarea/asjc/1600/1606 name=Physical and Theoretical Chemistry /dk/atira/pure/subjectarea/asjc/1600/1604 name=Inorganic Chemistry /dk/atira/pure/subjectarea/asjc/2500/2505 name=Materials Chemistry
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...
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