Desulfurative Functionalization of β-Acyl Allylic Sulfides with N–H Free Indoles Highly Regioselective at C3 and N1 Positions: Rapid Access to α-Branched Enones DOI

Qin-Qin Dang,

Xue-Ni Liu,

Hui Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5200 - 5206

Published: March 19, 2024

A regiodivergent allylation of 1H-indoles highly selectively at the C3 and N1 positions with β-acyl allylic sulfides through desulfurative C–C/C–N bond-forming reactions has been developed under mild conditions. Notably, remarkable site-selective switch can be achieved by a delicate choice solvents bases. This cost-efficient method displays broad substrate scope, good functional compatibility, excellent site-selectivity, thus offering divergent synthesis indole substituted α-branched enones, which possess diverse potential opportunities for further applications derivatization.

Language: Английский

Transition metal-catalyzed cross-coupling reactions of N-aryl-2-aminopyridines DOI Creative Commons
Fatemeh Doraghi,

Lina Rezainia,

Mohammad Hossein Morshedsolouk

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(2), P. 1134 - 1151

Published: Jan. 1, 2025

Due to the presence of pyridyl directing group, N-aryl-2-aminopyridines can quickly form stable complexes with metals, leading cyclization and functionalization reactions. A large number N-heterocycles nitrogen-based molecules be easily constructed via this direct atom-economical cross-coupling strategy. In review, we have highlighted transformations in various transition metal catalysts, such as palladium, rhodium, iridium, ruthenium, cobalt copper.

Language: Английский

Citations

1

Access to Benzyl Oxindoles via Electron Donor‐Acceptor Complex Photoactivation Using Thianthrenium Salts and Potassium Carbonate DOI
Pau Sarró, Albert Gallego‐Gamo, Roser Pleixats

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2587 - 2595

Published: April 19, 2024

Abstract A photochemical synthesis of biologically relevant benzyl oxindoles is presented via electron‐donor acceptor (EDA) complex strategy. This exogenous photocatalyst‐free method describes the formation a new electron donor‐acceptor based on potassium carbonate and thianthrenium salts for C( sp 2 )−C( 3 ) bond formation. transition‐metal free reaction allows rapid increase in molecular complexity chemical space, tolerating different functional groups as well sophisticated biomolecules. The scalability sustainability this highlighted by an important waste recovery protocol. Mechanistic investigations support EDA that induces radical chain, applicability showcased straightforward derivatization reactions.

Language: Английский

Citations

7

Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents DOI
Jia‐Lin Tu, Binbin Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Language: Английский

Citations

6

Catalytic asymmetric synthesis of sulfur-containing atropisomers by C-S bond formations DOI Open Access

Ren‐Fei Cao,

Zhi‐Min Chen

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(12), P. 3331 - 3346

Published: Nov. 17, 2023

Language: Английский

Citations

12

Recent advance: Sulfur ylides in organic synthesis DOI
M. Kumar,

Ifrah Sadaf,

Jyotsna Pamidighantam

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2023, Volume and Issue: 61(1), P. 29 - 70

Published: Oct. 26, 2023

Abstract Sulfur ylides are versatile structures that display various characteristics and participate in a myriad of reactions to produce simple, effective, sometimes stereoselective toward synthesizing sulfur‐containing compounds. Nonetheless, their fulfillment tremendous developments have been made this field the past few decades. In comprehensive review, luminosity is illuminated on application sulfur involved domino, cascade annulation reactions, carbene trapping reagents with chameleonic reactivity. numerous decennary, chemists used solvent‐dependent, rhodium catalyzed, dealkylative intercepted, photochemical reaction, halotrifluoromethylation, benzannulation, amidation name such as Mizoroki–Heck, Suzuki–Miyaura, Sommelet–Hauser rearrangements. Moreover, other prime applications include metal catalysis, epoxidation carbonyl compounds, acylmethylation, cyclomerization, oxidation, insertion reactions. Additionally, some extremely useful play major role synthesis medicinally active heterocycles structural motifs. This review article discusses all these proposed mechanisms, current scenario, at length. tutorial concludes by providing future outlook investigation into compounds synthesized using it great potential be industries, laboratories, pharmaceutical companies, drug production, clinical use, medicinal chemistry, agrochemical purposes.

Language: Английский

Citations

11

Palladium(II) NCS‐Pincer Complexes Mediated Regioselective Cross Dehydrogenative Alkenation of 2‐Arylthiophenes DOI
Sohan Singh, Suman Mahala,

Nattamai Bhuvanesh

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(15)

Published: March 18, 2024

Abstract In this report, we have synthesized two new NCS pincer ligands by the Schiff base reaction of 3‐((phenylthio)methoxy)benzaldehyde ( P ) with alkyl amines t butylamine L1 and 1‐adamantylamine L2 )). The palladium complexes butylamine= C1 1‐adamantylamine= C2 these were their PdCl 2 (CH 3 CN) precursor. newly characterized using various analytical spectroscopic techniques such as 1 H, 13 C{ H} Nuclear Magnetic Resonance (NMR), Ultraviolet–visible (UV‐Visible), Fourier Transform Infrared (FTIR) Spectroscopy, High‐Resolution Mass Spectrometry (HRMS). structure ligand its coordination mode precursor studied help single‐crystal X‐ray diffraction. showed distorted square planar geometry around center. used catalysts for regioselective cross‐dehydrogenative alkenation 2‐arylthiophene derivatives. complex , where sterically bulky adamantyl is part side arm a higher yield reaction. Only 2.5 mol% catalyst loading was sufficient to achieve 74–95 % yields desired products excellent functional group tolerance under mild conditions. poisoning experiments (PPh Hg) homogeneous nature catalytic process. plausible mechanism proposed based on control time‐dependent HRMS studies.

Language: Английский

Citations

4

Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation DOI
Sichang Wang, Liting Wang, Jin Cui

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.

Language: Английский

Citations

0

Recent Advancement on Selectfluor Mediated Synthesis of Heterocyclic Molecules DOI Open Access
Sukanya Das, Rudra Narayan Das, Tapas Ghosh

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 16, 2025

Abstract Selectfluor, [1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)], is a highly valuable reagent in contemporary chemistry, serving not only as an electrophilic fluorinating agent but also effective catalyst the synthesis of various pharmaceutically relevant heterocycles. This review article seeks to present comprehensive overview significant heterocyclic ring formations facilitated by selectfluor. Both metal‐free and metal‐catalyzed recent advancement on selectfluor mediated cyclisation processes are discussed this mainly over last eight years (2017‐April 2024).

Language: Английский

Citations

0

Synthesis, electrochemical and quantum chemical studies of new pyrido[2,3-d]pyrimidine derivatives incorporating sulfonamide moiety DOI
Huda A. Al‐Ghamdi,

Esam A. Ishak,

Hamdi M. D. Nasr

et al.

Journal of the Iranian Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Language: Английский

Citations

0

Sulfoxides as electrophilic substrates in cross-coupling reactions DOI
Rahadian Zainul, Bahaa Fadhil Hamzah, Hussein Ali Al‐Bahrani

et al.

Journal of Sulfur Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 14

Published: Feb. 25, 2025

Language: Английский

Citations

0