Cargando…

Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines

[Image: see text] A metal-free scalable synthesis of functionalized ketenimines from alkyl α-(aryl/heteroaryl)-α-diazoacetates and alkyl isocyanides induced by blue light irradiation has been developed. The reaction proceeds at room temperature without any photocatalyst and provides ketenimines in m...

Descripción completa

Detalles Bibliográficos
Autores principales:	Sakharov, Pavel A., Novikov, Mikhail S., Nguyen, Tuan K., Kinzhalov, Mikhail A., Khlebnikov, Alexander F., Rostovskii, Nikolai V.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2022
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8928522/ https://www.ncbi.nlm.nih.gov/pubmed/35309460 http://dx.doi.org/10.1021/acsomega.2c00367

Ejemplares similares

Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
por: Sakharov, Pavel A., et al.
Publicado: (2022)

Stereoselective Bioreduction of α-diazo-β-keto Esters
por: González-Granda, Sergio, et al.
Publicado: (2020)

Triethylamine-Promoted Oxidative Cyclodimerization of 2H-Azirine-2-carboxylates to Pyrimidine-4,6-dicarboxylates: Experimental and DFT Study
por: Zakharov, Timofei N., et al.
Publicado: (2023)

Z-Selective iridium-catalyzed cross-coupling of allylic carbonates and α-diazo esters
por: Thomas, Bryce N., et al.
Publicado: (2017)

Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization
por: Rostovskii, Nikolai V, et al.
Publicado: (2015)

Triarylborane‐Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds
por: Dasgupta, Ayan, et al.
Publicado: (2020)

5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids
por: Agafonova, Anastasiya V., et al.
Publicado: (2022)

Visible-light-promoted N–H functionalization of O-substituted hydroxamic acid with diazo esters
por: Xia, Shuangshuang, et al.
Publicado: (2023)

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
por: Rajeev, Narasimhamurthy, et al.
Publicado: (2020)

Enantiopure β-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions
por: Manenti, Marco, et al.
Publicado: (2022)

High-Level Rovibrational Calculations on Ketenimine
por: Tschöpe, Martin, et al.
Publicado: (2021)

Non-natural 2H-azirine-2-carboxylic acids: an expedient synthesis and antimicrobial activity
por: Sakharov, Pavel A., et al.
Publicado: (2019)

Studies of Nature of Uncommon Bifurcated I–I···(I–M) Metal-Involving Noncovalent Interaction in Palladium(II) and Platinum(II) Isocyanide Cocrystals
por: Bulatova, Margarita, et al.
Publicado: (2021)

α-Diazo-λ(3)-iodanes and α-diazo sulfonium salts: the umpolung of diazo compounds
por: Timmann, Sven, et al.
Publicado: (2023)

Synthesis of Highly Reactive Ketenimines via Photochemical Rearrangement of Isoxazoles
por: Bracken, Cormac, et al.
Publicado: (2023)

Discovery of tert-Butyl Ester Based 6-Diazo-5-oxo-l-norleucine Prodrugs for Enhanced Metabolic Stability and Tumor Delivery
por: Novotná, Kateřina, et al.
Publicado: (2023)

Captodative Formyl Enamines in a New Synthesis of Tertiary α-Amino Esters
por: Rulev, Alexandre Yu., et al.
Publicado: (2001)

Copper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters
por: Li, Zhengning, et al.
Publicado: (2015)

Lipase-Catalyzed Chemoselective Ester Hydrolysis of Biomimetically Coupled Aryls for the Synthesis of Unsymmetric Biphenyl Esters
por: Ehlert, Janna, et al.
Publicado: (2019)

Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4-phthalimidocarboxylic esters derived from methionine and cysteine
por: Enßle, Marc, et al.
Publicado: (2012)

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
por: Xiong, Yiwen, et al.
Publicado: (2014)

Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters
por: Guan, Weiye, et al.
Publicado: (2014)

Porous Organic Polymer Synthesized by Green Diazo-Coupling Reaction for Adsorptive Removal of Methylene Blue
por: Shen, Yang, et al.
Publicado: (2021)

Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow
por: Lima, Fabio, et al.
Publicado: (2016)

Copper-catalyzed Z-selective synthesis of acrylamides and polyacrylamides via alkylidene ketenimines
por: Duan, Xuelun, et al.
Publicado: (2022)

A Lewis Acid Stabilized Ketenimine in an Unusual Variant of the Electrophilic Aromatic Substitution
por: Surkau, Jonas, et al.
Publicado: (2022)

4-Dimethylaminopyridine-Catalyzed Metal-Free Aerobic Oxidation of Aryl α-Halo Esters to Aryl α-Keto Esters
por: Jung, Yeonghun, et al.
Publicado: (2020)

Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
por: Lou, Yazhou, et al.
Publicado: (2019)

Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds
por: Zhukovsky, Daniil, et al.
Publicado: (2022)

In vitro characterization of nonribosomal peptide synthetase-dependent O-(2-hydrazineylideneacetyl)serine synthesis indicates a stepwise oxidation strategy to generate the α-diazo ester moiety of azaserine
por: Shikai, Yusuke, et al.
Publicado: (2023)

Heterogeneous cellular effects of α-ketoglutarate esters
por: Galluzzi, Lorenzo
Publicado: (2019)

B(C(6)F(5))(3)-Catalyzed Diastereoselective and Divergent Reactions of Vinyldiazo Esters with Nitrones: Synthesis of Highly Functionalized Diazo Compounds
por: Stefkova, Katarina, et al.
Publicado: (2023)

Decarbonylative organoboron cross-coupling of esters by nickel catalysis
por: Muto, Kei, et al.
Publicado: (2015)

The halogen bond with isocyano carbon reduces isocyanide odor
por: Mikherdov, Alexander S., et al.
Publicado: (2020)

Synthesis of New Racemic α,α-Diaminocarboxylic Ester Derivatives
por: Houssine, Mabrouk El, et al.
Publicado: (2010)

Hepatic Retinyl Ester Hydrolases and the Mobilization of Retinyl Ester Stores
por: Grumet, Lukas, et al.
Publicado: (2016)

Synthesis and antimicrobial properties of 4-acylaminobenzenethiosulfoacid S-esters
por: Lubenets, Vira, et al.
Publicado: (2017)

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
por: Noble, Adam, et al.
Publicado: (2018)

Visible-light-mediated synthesis of oxime esters via multicomponent reactions of aldehydes, aryl amines, and N-hydroxyphthalimide esters
por: Nguyen, Anh Thu, et al.
Publicado: (2023)

α-Anilinoketones, Esters and Amides: A Chemical Study
por: Qandil, Amjad M., et al.
Publicado: (2012)

Cannot write session to /tmp/vufind_sessions/sess_bpghni4p0lumu6enm99upuue7s