Browsing by Author "Correa, Arkaitz"
Now showing items 1-20 of 26
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1, 2, 3 - Triazoles as key frameworks in drug discovery & metal catalysis
La tesis se enmarca dentro de la química de los 1H-1,2,3-triazoles y sus sales de N-alquil-triazolio. El trabajo realizado contempla los siguientes objetivos:1.- Sintetizar y estudiar los 1H-1,2,3-triazoles como plantillas ... -
Co-Catalyzed C(sp3)−H Oxidative Coupling of Glycine and Peptide Derivatives
San Segundo Eizaguirre, Marcos; Guerrero Azurmendi, Itziar; Correa Navarro, Arkaitz (American Chemical Society, 2017-09-22)obalt-catalyzed selectiveα-alkylation andα-heteroarylation processes ofα-amino esters and peptide derivativesare described. These cross-dehydrogenative reactions occur undermild conditions and allow for the rapid assembly ... -
Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides
The functionalization of typically unreactive C(sp3)–H bondsholds great promise for reducing the reliance on existing functionalgroups while improving atom-economy and energy efficiency. As a re-sult, this topic ... -
Cu-Catalyzed Site-Selective C(sp2)–H Radical Trifluoromethylation of Tryptophan Containing Peptides
Site-selective functionalization of C–H bonds within a peptide framework poses a challenging task of paramount synthetic relevance. Herein, we report an operationally simple C(sp2)–H trifluoromethylation of tryptophan ... -
Iron-Catalyzed C(sp3)−H Functionalization of N,N-Dimethylanilines with Isocyanides
Guerrero Azurmendi, Itziar; San Segundo Eizaguirre, Marcos; Correa Navarro, Arkaitz (Royal Society of Chemistry, 2018-01-22)An efficient ligand-free Fe-catalyzed oxidative Ugi-type reaction toward the assembly of α-amino amides and short peptides is described. The reaction proceeds through the α-C(sp3)−H oxidation of N,N-dimethylanilines and ... -
Iron-Catalyzed Direct α-Arylation of Ethers with Azoles
Correa Navarro, Arkaitz ; Fiser, Béla; Gómez Bengoa, Enrique (Royal Society of Chemistry, 2015-07-14)The direct α-arylation of cyclic and acyclic ethers with azoles has been achieved, which features a novel iron-catalyzed cross-dehydrogenative coupling (CDC) process. This practical oxidative method allowed the efficient ... -
Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
Urruzuno Guiu, Iñaki; Andrade Sampedro, Paula; Correa Navarro, Arkaitz (American Chemical Society, 2021-09-17)The selective tagging of amino acids within a peptide framework while using atom-economical C-H counterparts poses an unmet challenge within peptide chemistry. Herein, we report a novel Pd-catalyzed late-stage C-H acylation ... -
Merging Metal Catalysis & DFT Studies toward the C-H Functionalization of a-Amino Carbonyl Compounds.
Andrade Sampedro, Paula (2023-03-27)El principal objetivo de esta Tesis Doctoral consiste en el diseño de nuevos métodos catalíticos via funcionalización de enlaces C-H dirigidos a la modificación selectiva de aminoácidos y péptidos. En particular, se han ... -
Metal-Catalyzed C(sp2)−H Functionalization Processes of Phenylalanine- and Tyrosine-Containing Peptides
The site-selective chemical diversification of biomolecules constitutes an unmet challenge of capital importance within medicinal chemistry and chemical biology. The functionalization of otherwise unreactive C-H bonds holds ... -
Metal-catalyzed C–H functionalization processes upon “click”-triazole assistance
The functionalization of otherwise unreactive C–H bonds holds great promise for reducing the reliance on existing functional groups while improving energy efficiency and atom-economy. One of the most powerful strategies ... -
Ni- and Fe-Based Cross-Coupling Reactions. Editorial
The series Topics in Current Chemistry Collections presents critical reviews from the journal Topics in Current Chemistry organized in topical volumes. The goal of this thematic volume is to give the non-specialist reader, ... -
On the Mechanism of Cross-Dehydrogenative Couplings between N-Aryl Glycinates and Indoles: A Computational Study
Andrade Sampedro, Paula; Matxain Beraza, Jon Mattin ; Correa Navarro, Arkaitz (American Chemical Society, 2020-09-17)Despite the widespread use of cross-dehydrogenative couplings in modern organic synthesis, mechanistic studies are still rare in the literature and those applied to α-amino carbonyl compounds remain virtually unexplored. ... -
Palladium-Catalyzed Site-Selective C(sp2)−H Acetoxylation of Tyrosine-Containing Peptides
A Pd-catalyzed C(sp2)−H acetoxylation of Tyr-containing peptides is described. The method relies on the use of a removable 2-pyridyloxy group as directing group and is distinguished by its reliable scalability and easily ... -
Pd-Catalyzed C–H Alkoxycarbonylation of Phenethyl- and Benzylamines with Chloroformates as CO Surrogates
The site‐selective functionalization of C−H bonds within a complex molecule remains a challenging task of capital synthetic importance. Herein, an unprecedented Pd‐catalyzed C(sp2)−H alkoxycarbonylation of phenylalanine ... -
Pd-catalyzed site-selective C(sp(2))-H radical acylation of phenylalanine containing peptides with aldehydes
The site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed delta-C(sp(2))-H acylation of Phe containing peptides ... -
Pd-catalyzed site-selective C(sp2)–H radical acylation of phenylalanine containing peptides with aldehydes
The site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed delta-C(sp(2))-H acylation of Phe containing peptides ... -
Ru-Catalyzed C-H Hydroxylation of Tyrosine-Containing Di- and Tripeptides toward the Assembly of L-DOPA Derivatives
[EN] The development of catalytic tools for the late-stage modification of amino acids within a peptide framework is a challenging task of capital importance. Herein, we report a Ru-catalyzed C(sp(2))-H hydroxylation of a ... -
Selective C(sp2)−H Halogenation of "click" 4-Aryl-1,2,3-triazoles
Goitia, Asier; Gómez Bengoa, Enrique; Correa Navarro, Arkaitz (American Chemical Society, 2017-02-09)Selective bromination reactions of “click compounds” are described. Electron-neutral and electron-deficient arenes selectively undergo unprecedented Pd-catalyzed C–H ortho-halogenations assisted by simple triazoles as ... -
Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
The development of useful synthetic tools to label amino acids within a peptide framework for the ultimate modification of proteins in a late-stage fashion is a challenging task of utmost importance within chemical biology. ... -
Site-Selective C - H Functionalization of Amino Acids and Peptides Upon Radical Chemistry
San Segundo Eizaguirre, Marcos (2021-04-15)El objetivo de esta Tesis Doctoral ha sido desarrollar nuevas metodologías de modificación selectiva decompuestos peptídicos. Por un lado, hemos estudiado metales alternativos como el cobalto para lamodificación C-H selectiva ...