Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

Reported here is a catalytic redox-neutral geminal dual C-H functionalization of oxindoles with two distinct aromatics using anilines. The reaction proceeded through a pluripotent tetra-substituted alkene intermediate via an extended resonance stabilized carbocation. It furnished wide chemical space around oxindoles with the generation of all carbon quaternary centers (>35 examples) in good to excellent yields. The developed process is highly regioselective and scalable, and the conditions are environmentally benign in nature.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.5c00021DOI Listing

Publication Analysis

Top Keywords

carbon quaternary
8
redox-neutral geminal
8
geminal dual
8
dual c-h
8
c-h functionalization
8
functionalization oxindoles
8
building carbon
4
quaternary center
4
center redox-neutral
4
oxindoles reported
4

Similar Publications

HO and CO Sorption in Ion-Exchange Sorbents: Distinct Interactions in Amine Versus Quaternary Ammonium Materials.

ACS Appl Mater Interfaces

September 2025

The Steve Sanghi College of Engineering, Mechanical Engineering, Northern Arizona University, Flagstaff, Arizona 86011, United States.

This study investigates the HO and CO sorption behavior of two chemically distinct polystyrene-divinylbenzene-based ion exchange sorbents: a primary amine and a permanently charged strong base quaternary ammonium (QA) group with (bi)carbonate counter anions. We compare their distinct interactions with HO and CO through simultaneous thermal gravimetric, calorimetric, gas analysis, and molecular modeling approaches to evaluate their performance for dilute CO separations like direct air capture. Thermal and hybrid (heat + low-temperature hydration) desorption experiments demonstrate that the QA-based sorbent binds both water and CO more strongly than the amine counterparts but undergoes degradation at moderate temperatures, limiting its compatibility with thermal swing regeneration.

View Article and Find Full Text PDF

From Barren Rock to Thriving Life: How Nitrogen Fuels Microbial Carbon Fixation in Deglaciated Landscapes.

Environ Sci Technol

September 2025

Key Laboratory of Green Utilization of Critical Non-metallic Mineral Resources, Ministry of Education, Wuhan University of Technology, Wuhan 430070, China.

Rapidly expanding nascent ecosystems at glacier forefields under climate warming dramatically enhance the terrestrial carbon (C) sink. Microbial C fixation and degradation, closely implicated in nitrogen (N) transformation and plant-soil-microbe interactions, significantly regulate soil C accumulation. However, how shifts in microbial functional potential impact soil C sequestration during vegetation succession remains unclear.

View Article and Find Full Text PDF

The growing threat of antibiotic-resistant bacteria continues to be one of the biggest challenges facing public health. As a result, there is an increasing focus on developing new substances with both antimicrobial and biofilm inhibition activities. One such group of compounds is surfactants, particularly quaternary ammonium salts (QASs), which are commonly used as disinfectants in healthcare.

View Article and Find Full Text PDF

Evaluation of novel surfactants for the decontamination of chemical warfare agents.

Toxicol Mech Methods

September 2025

Department of Toxicology and Military Pharmacy, Military Faculty of Medicine, Hradec Kralove, University of Defence, Brno, Czech Republic.

The decontamination of chemical warfare agents or compounds involved in chemical industry incidents poses a significant challenge to environmental protection and human health. These compounds are highly toxic and could be relatively resistant to conventional decontamination methods. In recent years, surfactants have emerged as a promising option, as they can enhance the solubility of organophosphorus compounds in aqueous solutions while promoting their degradation or adsorption onto surfaces.

View Article and Find Full Text PDF

Enantioselective Incorporation of Amine Fragments onto Quaternary Carbons via Metallaphotoredox Catalysis.

Angew Chem Int Ed Engl

September 2025

State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.

The enantioselective construction of quaternary carbon stereocenters bearing amine functionalities represents a significant challenge in organic synthesis despite their prevalence in pharmaceutically active compounds. Herein, we report a versatile metallaphotoredox platform for the asymmetric incorporation of amine fragments onto quaternary carbons via coupling of alkene-tethered aryl bromides with readily available α-silylamines. This transformation proceeds under mild conditions without requiring organometallic reagents or stoichiometric reductants.

View Article and Find Full Text PDF