Electrocatalytic Enantioselective Tandem C–H Indolization toward Biindolyl Atropisomers: Reaction Development and Mechanistic Insight

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1422 - 1430

Published: Jan. 9, 2025

The electrochemical methods for asymmetric indolization are still elusive and pose a significant challenge. Taking advantage of 2-alkynylanilines as electrochemically compatible indolyl equivalents, we herein represent mild highly enantioselective electrocatalytic process tandem C–H to form 2,3′-biindolyl atropisomers along with hydrogen evolution reaction. Integrated experimental computational mechanistic studies revealed that sequential metalation/nucleophilic cyclization/reductive elimination/anodic oxidation sequence involving RhIII–RhI–RhIII catalytic cycle accounts the established transformation.

Language: Английский

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Navigating Electrochemical Oxidative Functionalization of Olefins: Selected Mechanistic and Synthetic Examples

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This highlight presents curated examples illustrating diverse electrochemical olefin functionalization strategies, including direct, mediated, and catalytic approaches, offering a concise overview of this rapidly evolving field.

Language: Английский

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N–N Atropisomer Synthesis via Electrolyte- and Base-Free Electrochemical Cobalt-Catalysed C–H Annulation

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(23), P. 11524 - 11530

Published: Jan. 1, 2024

An exogenous electrolyte- and base-free electrochemical cobalt-catalysed atroposelective C–H annulation has been established to construct N–N axially chiral isoquinolinones in excellent enantioselectivities good yields.

Language: Английский

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Atroposelective Synthesis of Biaryl N‐Oxides via Cu‐Catalyzed De Novo Heteroaromatic N‐Oxide Ring Formation

Advanced Science, Journal Year: 2024, Volume and Issue: 11(40)

Published: Aug. 9, 2024

Abstract Heteroaromatic N ‐oxides, renowned for their highly polar N─O bond and robust structure, exhibit significant bioactivities have played a pivotal role in various drug development projects since the discovery of Minoxidil. Moreover, heteroaromatic featuring axially chiral biaryl frameworks, are indispensable as Lewis base catalysts ligands organic synthesis. Despite importance, synthesizing these compounds is challenging, necessitating starting materials or resolution processes. Catalytic strategies rely on functionalization ‐oxide compounds, leading to products with relatively limited skeletal diversity. This study introduces Cu‐catalyzed atroposelective method ‐oxides via de novo ring formation. mild efficient approach achieves excellent stereoselectivities (up 99:1 er), enabling production wide array novel scaffolds. The product 3f demonstrates high stereoselectivity recyclability catalyst. Additionally, 3e exhibits promising therapeutic efficacy against triple‐negative breast cancer, IC 50 values 4.8 5.2 µ m MDA‐MB‐231 MDA‐MB‐468 cells, respectively. research not only advances synthesis challenging but also encourages further exploration entities bioactive small molecules.

Language: Английский

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Construction of Lactones via Ligand-Enabled Ni-Catalyzed Alkene Hydroxylarylation/Lactonization

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 19, 2024

Here, we report the preparation of lactones via Ni-catalyzed alkene hydroxylarylation and sequential intramolecular lactonization with O

Language: Английский

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Precisive Incorporation of Multiple Nitrogen Sources into Benzoxazoles via an Iodine-Mediated Electrochemical Four-Component Reaction

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

An iodine-mediated electrochemical four-component reaction was developed to construct aromatic C-N bonds by making use of a simple nitrogen source, such as NH

Language: Английский

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Rhodaelectro-Catalyzed Synthesis of Pyrano[3,4-b]indol-1(9H)-ones via the Double Dehydrogenative Heck Reaction between Indole-2-carboxylic Acids and Alkenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

A rhodaelectro-catalyzed double dehydrogenative Heck reaction of indole-2-carboxylic acids with alkenes has been developed for the synthesis pyrano[3,4-

Language: Английский

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