Chalcogen-containing and Chalcogen-functionalized Heterocycles DOI
Filipe Penteado, Eduardo E. Alberto

The Royal Society of Chemistry eBooks, Journal Year: 2023, Volume and Issue: unknown, P. 147 - 167

Published: Feb. 15, 2023

Heterocycles containing chalcogens as heteroatoms or embedded in several different functional groups founded interesting applications medicinal chemistry, coordination and materials. Recent development on their preparation is reported here.

Language: Английский

Transition-metal-free C–S bond cleavage and transformation of organosulfur compounds DOI
Ke Yang, Qin Li, Zhengyi Li

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(36), P. 5343 - 5364

Published: Jan. 1, 2023

The activation and transformation of organic chemical bonds is a fundamental scientific problem. In the past several decades, C-S bond cleavage for construction C-C C-heteroatom has received tremendous attention in chemistry. Although significant progress been made field transition metal strategies, variety novel transition-metal-free strategies have also developed using halogenated reagents, oxidants, acids, bases. Moreover, photochemical electrochemical methods to achieve organosulfur compounds. To date, however, no comprehensive review reported. Therefore, we herein provide major advances compounds, including thioethers, sulfoxides, sulfones, thioacetals, sulfonium salts, sulfur ylides.

Language: Английский

Citations

42

Photocatalytic functionalizations of alkynes DOI

Neha Chalotra,

Jaswant Kumar,

Tahira Naqvi

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(86), P. 11285 - 11300

Published: Jan. 1, 2021

Visible light mediated functionalizations have significantly expanded the scope of alkynes by unraveling new mechanistic pathways and enabling their transformation to diverse structural entities. The photoredox reactions on rely innate capability generate myriad carbon-centred radicals via single electron transfer (SET), thereby, allowing introduction radical precursors. Moreover, an array methods been developed facilitating transformations such as vicinal or gem-difunctionalization, annulation, cycloaddition oxidative construct numerous key building blocks natural pharmaceutically important molecules. In addition, chemistry has successfully used deal with challenges associated alkyne functionalization stereoselective regioselective control. This article accounts for several visible alkynes, wherein they transformed into α-oxo compounds, β-keto sulfoxides, substituted olefins, N-heterocycles, internal sulfur containing compounds. primarily categorized various sections based reaction type particular attention being paid details, advancement future applications.

Language: Английский

Citations

51

Trifluoromethylations of (Hetero)arenes and Polarized Alkenes Using Trifluoroacetic Anhydride under Photoredox Catalysis DOI
Yang Song,

Baihui Zheng,

Shuo Yang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2372 - 2376

Published: March 27, 2023

A novel trifluoromethylation of (hetero)arenes and polarized alkenes using simple trifluoroacetic anhydride (TFAA) as the low price CF3 source under photoredox catalysis was developed without additives such bases, hyperstoichiometric oxidant, or auxiliaries. The reaction showed excellent tolerance, including to some important natural products prodrugs, even on gram scale extended ketones. This protocol provides a practical utilization TFAA. Several perfluoroalkylations trifluoromethylation/cyclizations were successfully achieved identical conditions.

Language: Английский

Citations

22

Regioselective Photocatalytic Dialkylation/Cyclization Sequence of 3‐Aza‐1,5‐dienes: Access to 3,4‐Dialkylated 4‐Pyrrolin‐2‐ones DOI
Xiao Hu,

Minglin Tao,

Zhongxiao Ma

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(13), P. 2163 - 2168

Published: June 3, 2022

Abstract A visible‐light‐induced regioselective tandem enamido β‐C( sp 2 )−H alkylation/acrylamido alkylation/cyclizative alkenylation sequence of 3‐aza‐1,5‐dienes is presented. This protocol regiospecific, features a broad substrate scope, and provides direct access to 3,4‐dialkylated 4‐pyrrolin‐2‐ones from readily available N ‐alkenylacrylamides. It scalable gram scale, could be induced by natural sunlight. magnified image

Language: Английский

Citations

23

Exploring the regioselectivity of the cyanoalkylation of 3-aza-1,5-dienes: photoinduced synthesis of 3-cyanoalkyl-4-pyrrolin-2-ones DOI

Jia-Qin He,

Zhixian Yang,

Xue-lu Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4575 - 4582

Published: Jan. 1, 2022

Regioselective cyanoalkylalkenylation of 3-aza-1,5-dienes with oxime esters induced by visible light.

Language: Английский

Citations

21

Medicinal chemistry-based perspective on thiophene and its derivatives: Exploring the structural insights to discover plausible druggable leads DOI
Shikha Thakur, Devendra Kumar, Shivani Jaiswal

et al.

RSC Medicinal Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 31, 2024

Thiophene is a privileged pharmacophore in medicinal chemistry owing to its diversified biological attributes.

Language: Английский

Citations

4

[2,3] Sigmatropic Rearrangement of Allylic S-Acylsulfonium Ylide Intermediates Generated from Rhodium-Catalyzed Addition of Diazo Compounds DOI

C. M. CRIBBS,

Jason R. Combs,

Viktor Gevirtzman

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Allyl thioesters, thiocarbonates, thiocarbamates, and thiocyanates are shown to undergo rhodium-catalyzed addition of carbene groups, generated from diazo compounds, afford S-acyl sulfonium ylides that [2,3] sigmatropic rearrangement. Competing side reactions such as cyclopropanation [1,2] acyl shifts not observed. The reaction works with a variety sulfur functional including thiocyanates, affording densely functionalized products. well trimethylsilyldiazomethane (TMSD) α-aryl diazoesters.

Language: Английский

Citations

0

Photoinduced Synthesis and Functionalization of Fused Thiophenes DOI
Yuanyuan Sun, Yinsong Zhao, Xuefeng Jiang

et al.

Topics in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

Electroreductive synthesis of polyfunctionalized pyridin-2-ones from acetoacetanilides and carbon disulfide with oxygen evolution DOI
Li-Chun Xu,

Zhongxiao Ma,

Xi Hu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(5), P. 1013 - 1018

Published: Jan. 1, 2022

A reductant-free electroreductive synthesis of polyfunctionalized pyridin-2-ones under the combined action electro/copper/base with O 2 evolution.

Language: Английский

Citations

12

Synthesis of Sulfonimidamide‐Based 1,2‐Benzothiazines by [4+2] Oxidative Annulation of Sulfonimidamides and Alkynes in Water under Visible Light DOI

N. Karthikeyan,

S. Ravindra,

V. R. Padma Priya

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(6)

Published: Jan. 5, 2024

Abstract Herein, we disclose a visible‐light‐induced rhodium‐catalyzed oxidative C−H/N−H bond activation of sulfonimidamides (SIAs) and subsequent [4+2] annulation with an alkyne in water to yield SIA‐based 1,2‐benzothiazines good high yields short reaction times. Further, the C=C benzothiazine can be cleaved under environmentally friendly conditions (oxygen atmosphere blue LEDs) deliver o ‐acyl‐ N ‐acyl SIAs. Interestingly, SIAs also synthesized directly from very without isolating benzothiazine. The selective efficient reduction presence InCl 3 /R SiH led formation hitherto unknown dihydro‐1,2‐benzothiazine quantitative yield.

Language: Английский

Citations

2