Concept

Electrophilic aromatic substitution

Related publications (32)

Organocatalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoesters: Development and Application to the Total Synthesis of (+)‐Alstratine A

Qian Wang, Jieping Zhu, Rémi Julien Sylvain Andres, Fenggang Sun

We report herein an asymmetric Pictet– Spengler reaction of α-ketoesters. In the presence of a catalytic amount of simple alanine-derived squaramide and p-nitrobenzoic acid, reaction of tryptamines with methyl 2-oxoalkanoates afforded the corresponding 1- ...

2023

Monitoring On-Target Signaling Responses in Larval Zebrafish- Z-REX Unmasks Precise Mechanisms of Electrophilic Drugs and Metabolites

Yimon Aye, Jesse Poganik, Kuan-Ting Huang, Phillippe Ly

Reactive metabolites and related electrophilic drugs are among the most challenging small molecules to study. Conventional approaches to deconstruct the mode of action (MOA) of such molecules leverage bulk treatment of experimental specimens with an excess ...

JOURNAL OF VISUALIZED EXPERIMENTS2023

Semipinacol Rearrangement of Cyclopropenylcarbinols for the Synthesis of Highly Substituted Cyclopropanes

Jérôme Waser, Vladyslav Smyrnov

An electrophile-induced semipinacol rearrangement of cyclopropenylcarbinols is reported. This transformation gives access to various polyfunctionalized cyclopropanes under mild metal-free conditions. The scope of the reaction includes iodine, sulfur and se ...

2023

Chlorination of amides: Kinetics and mechanisms of formation of N-chloramides and their reactions with phenolic compounds

Urs von Gunten, Tianqi Zhang

Amides are common constituents in natural organic matter and synthetic chemicals. In this study, we investi-gated kinetics and mechanisms of the reactions of chlorine with seven amides, including acetamide, N-meth-ylformamide, N-methylacetamide, benzamide, ...

2023

Ni-Based Nanoparticles Catalyzed Hydrodeoxygenation of Ketones, Ethers, and Phenols to (Cyclo) Aliphatic Compounds

Paul Joseph Dyson, Mingyang Liu, Xiang Li, Yelin Hu, Matthias Beller

Catalytic hydrodeoxygenation is of prime importance in the valorization of biomass-based feedstocks to produce essential chemicals and fuels. To carry out this process in a more cost-effective and sustainable manner, the use of 3D-metal-based nanostructure ...

Washington2023

TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent

Dina Boyarskaya

Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...

EPFL2023

Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B

Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe

Transition-metal-catalyzed [4+2] heteroannulation of alpha,beta-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically su ...

WILEY-V C H VERLAG GMBH2023

The Mononuclear Metal-Binding Site of Mo-Nitrogenase Is Not Required for Activity

Wenyu Gu

The biological N-2-fixation process is catalyzed exclusively by metallocofactor-containing nitrogenases. Structural and spectroscopic studies highlighted the presence of an additional mononuclear metal-binding (MMB) site, which can coordinate Fe in additio ...

Washington2023

Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling

Paul Joseph Dyson, Mingyang Liu

Efficient valorization of lignin, a sustainable source of functionalized aromatic products, would reduce dependence on fossil-derived feedstocks. Oxidative depolymerization is frequently applied to lignin to generate phenolic mono- mers. However, due to th ...

2023

A Simple, Transition Metal Catalyst-Free Method for the Design of Complex Organic Building Blocks Used to Construct Porous Metal-Organic Frameworks

Wendy Lee Queen, Jordi Espin Marti, Till Marian Schertenleib, Nazanin Taheri, Ilia Kochetygov, Anita Justin, Jocelyn Richard Roth, Sophia Alessandra Pache

The design of metal-organic frameworks (MOFs) having large pore sizes and volumes often requires the use of complex organic ligands, currently synthesized using costly and time-consuming palladium-catalyzed coupling chemistry. Thus, in the present work, a ...

WILEY-V C H VERLAG GMBH2023

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