Discovery of EDA‐Complex Photochemical Reactions Using Computational Vision DOI
Rodrigo C. Silva, Gabriel M. F. Batista, Timothy J. Brocksom

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract Herein, we report a multidimensional screening strategy to discover Electron Donor‐Acceptor (EDA) complex photochemical reactions using only simple photographic devices, such as webcams or cellphones, combined with TLC analysis. An algorithm was designed automatically identify EDA‐complex reactive mixtures in solution by processing digital images from 96‐well microplate, alongside results. The code detects the absorption region of mixture visible spectrum and quantifies color changes through grayscale values. Integrated automatic analysis further classifies colorimetric reactions, non‐reactive, potentially EDA complexes. Leveraging this platform, have developed new EDA‐mediated approach synthesize iminophosphoranes yields up 90%.

Language: Английский

Electroreductive Remote Benzylic C(sp3)–H Arylation of Aliphatic Ethers Using Cyanoarenes for the Synthesis of α-(Hetero)aryl Ethers DOI

Liang Zeng,

Hua-Zhan Ren,

Gui‐Fen Lv

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2440 - 2444

Published: March 19, 2024

An iodoarene-driven electroreductive remote C(sp3)–H arylation of unsymmetrical 1-(o-iodoaryl)alkyl ethers with cyanoarenes for the site selective synthesis α-(hetero)aryl is developed. With introduction as both aryl sources and electron transfer mediators, this method includes an strategy to enable regiocontrollable formation two new bonds, one C(sp2)–H bond, C(sp2)–C(sp3) in a single reaction step through sequence halogen atom (XAT), hydrogen (HAT), radical–radical coupling, decyanation.

Language: Английский

Citations

11

Photochemical and Electrochemical Synthesis of Oxazoles and Isoxazoles: An Update DOI
Debashis Ghosh,

Ancy Sherin,

Sumit Ghosh

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2186 - 2208

Published: April 4, 2024

Abstract This review presents an outline of current advancements in the photochemical and electrochemical synthesis oxazoles isoxazoles. Oxazole isoxazole are important building blocks for a variety medicinally useful compounds. Therefore, these heterocycles via sustainable technologies is worth demanding. Photochemical two among few technologies. covers brief discussion on reaction parameters like catalysts, substrates scope, temperature, solvents, electrodes, electrolytes (in case process), light source process) individual reaction. Detailed mechanistic insight each also presented. Finally, summary, future direction toward development effective methods isoxazoles

Language: Английский

Citations

10

Visible-Light-Promoted Metal- and Photocatalyst-Free Reactions between Arylglyoxylic Acids and Tetraalkylthiuram Disulfides: Synthesis of α-Ketoamides DOI
Subhankar Kumar Sarkar, Satyajit Pal, Anindita Mukherjee

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1473 - 1482

Published: Jan. 16, 2024

A convenient and new synthetic approach has been developed for the oxidative cross-coupling of C–N bond through reaction between arylglyoxylic acids tetraalkylthiuram disulfides. The proceeds under ambient air at room temperature in presence visible light. This offers a metal-, base-, photocatalyst-, solvent-free synthesis various α-ketoamides with moderate to excellent yields via radical pathway. In addition, this protocol demonstrates potential application gram-scale synthesis.

Language: Английский

Citations

9

Alcohols as Alkyl Synthons Enabled by Photoredox-Catalyzed Deoxygenative Activation DOI

Tanumoy Mandal,

Samrat Mallick,

Malekul Islam

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(17), P. 13451 - 13496

Published: Aug. 26, 2024

Alcohols are abundant with versatile structural variety and have ample use as pivotal functional groups in numerous organic processes. Because of their frequent occurrence enumerable natural products, bioactive molecules, medicinal components, alcohol functionalities provide a promising scope research to advance the operational diversity for improving clinical success. Recent years witnessed design modern C–C C–heteroatom bond-forming approaches easily accessible commercially available unactivated aliphatic alcohols native adaptive sp3 handles, hence offering groundbreaking transformative pathways functionalization complex molecular architectures. The judicial application appropriate activating generate alkyl radical from through C–O bond fragmentation employ it potential alkylating agent unfolds unique synthetic strategies, thereby replacing obvious requirement halides. This review elaborately discusses recent trends regarding using C(sp3)-centered various chemical transformations by exploiting different activation modes disrupter under photoredox catalysis. presentation is organized nature scaffolds, kind formation, progress achieved this domain since original discovery providing illustrative examples mechanistic details, focus on difficulties future prospects.

Language: Английский

Citations

8

Visible‐light Induced C‐3 Carbamoylation of Quinoxalinones Assisted by EDA Complex DOI

Aznur Azim,

Tanumoy Mandal,

Vidhul Vasudevan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: June 13, 2024

Abstract A visible‐light‐promoted strategy for the decarboxylative C‐3 carbamoylation of quinoxalinone scaffolds is developed. This approach initiates through formation an EDA complex between oxamic acid and quinoxalinone. Successive SET construct C−C bond. method utilizes aerial oxygen as green oxidant eradicates process from use external photocatalysts transition metals. Detailed synthetic photophysical studies enlighten reaction pathway.

Language: Английский

Citations

4

Visible‐Light‐Induced Three‐Component Alkylpyridylation of Alkenes Enabled by Electron Donor‐Acceptor Complex DOI
Jiaxuan Shen, Meijun Chen, Jincan Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(14), P. 3138 - 3143

Published: May 11, 2024

Abstract Visible‐light‐induced difunctionalization of alkenes is a powerful strategy for constructing complex molecules. Herein, we disclose three‐component 1,2‐alkylpyridylation under mild and photosensitizers‐free conditions. UV‐vis absorption spectroscopy studies NMR titration experiments indicate that the formation an EDA between 4‐alkyl‐DHPs 4‐cyanopyridines. Primary, secondary, tertiary C( sp 3 )‐centered radicals were formed by homolytic cleavage 4‐alkyl‐DHPs. Gram‐scale synthesis late‐stage functionalization medicinally relevant molecules showed synthetic potential our methodology.

Language: Английский

Citations

3

Earth‐Abundant Recyclable Magnetic Iron Oxide Nanoparticles for Green‐light Mediated C−H Arylation in Heterogeneous Phase DOI

Tanumoy Mandal,

Ashwin Chaturvedi,

Aznur Azim

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: May 24, 2024

A magnetically isolable iron oxide nanoparticles is introduced as an efficient heterogeneous photocatalyst for non-directed C-H arylation employing aryl diazonium salts the precursors. This first-row transition metal-based revealed versatile activities and applicable to a wide range of substrates, demonstrating brilliant efficacy superior recyclability. Detailed catalytic characterization describes physical properties redox behavior Fe-catalyst. Adequate control experiments helped establish radical-based mechanism arylation.

Language: Английский

Citations

3

Iodine(iii)-promoted oxidative carbotrifluoromethylation of maleimides with imidazopyridines and Langlois’ reagent DOI

Dipti Lai,

Suvam Bhattacharjee,

Saurodeep Mandal

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(16), P. 2232 - 2235

Published: Jan. 1, 2024

Herein, we report a metal-free protocol for oxidative carbotrifluoromethylation of maleimides with imidazopyridines and Langlois’ reagent using PIDA as an oxidant.

Language: Английский

Citations

2

C─H Functionalization of Heteroarenes via Electron Donor‐Acceptor Complex Photoactivation DOI
Alakananda Hajra,

Madhusudan Mondal,

Sumit Ghosh

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: July 8, 2024

C-H Functionalization of heteroarenes stands as a potent instrument in organic synthesis, and with the incorporation visible light, it emerged transformative game-changer. In this domain, electron donor-acceptor (EDA) complex, formed through pairing an electron-rich substrate electron-accepting molecule, has garnered substantial consideration recent years due to related avoidance requirement photocatalyst well oxidant. EDA complexes can undergo photoactivation under mild conditions exhibit high functional group tolerance, making them potentially suitable for functionalization biologically relevant heteroarenes. This review article provides overview advancements field via complex literature coverage up April, 2024.

Language: Английский

Citations

2

Minisci-Type Dehydrogenative Coupling of C(sp3)–H and N-Heteroaromatics Enabled by Photoelectrochemical Hydrogen Atom Transfer DOI
Kaikai Qiao,

Yang Junfeng,

Zhi Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5805 - 5810

Published: July 1, 2024

Minisci-type dehydrogenative coupling of C(sp3)–H and N-heteroaromatics was performed with N-hydroxysuccinimide as a hydrogen atom transfer catalyst in photoelectrochemical cell composed mesoporous BiVO4 photoanode Pt electrode. In the absence metal catalysts chemical oxidants, range N-heteroarenes (e.g., quinolines, isoquinolines, quinoxaline) can undergo various partners to form corresponding products excellent yields.

Language: Английский

Citations

2