Light-mediated sulfonyl-iodination of ynamides and internal alkynes DOI
Mohana Reddy Mutra, Jing Li, Jeh‐Jeng Wang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(43), P. 6584 - 6587

Published: Jan. 1, 2023

We synthesized tetrasubstituted olefins regioselectively and stereoselectively from ynamides internal alkynes with sulfonyl iodides under blue LEDs in few minutes. The key features are being metal-free, easy to handle, simple, broad scope, environmentally friendly. Furthermore, a gram-scale experiment was conducted, the corresponding sulfonyl-iodinated products were smoothly altered into various other products.

Language: Английский

Recent advances in cascade radical cyclization of radical acceptors for the synthesis of carbo- and heterocycles DOI

Jianhua Liao,

Xiao Yang, Lu Ouyang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(6), P. 1345 - 1363

Published: Jan. 1, 2021

This review is devoted to highlighting main achievements in the development of cascade radical cyclization acceptors for synthesis carbo- and heterocycles.

Language: Английский

Citations

149

Recent advances in tandem selenocyclization and tellurocyclization with alkenes and alkynes DOI Open Access
Kai Sun, Xin Wang, Chao Li

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(19), P. 3100 - 3119

Published: Jan. 1, 2020

This review highlights recent progress in tandem selenocyclization and tellurocyclization with alkenes alkynes, an emphasis on the scopes, limitations mechanisms of these different reactions.

Language: Английский

Citations

141

Design principles of the use of alkynes in radical cascades DOI
Chaowei Hu,

Justice Mena,

Igor V. Alabugin

et al.

Nature Reviews Chemistry, Journal Year: 2023, Volume and Issue: 7(6), P. 405 - 423

Published: March 28, 2023

Language: Английский

Citations

53

Tandem construction of biological relevant aliphatic 5-membered N-heterocycles DOI
Daniel Łowicki, Piotr Przybylski

European Journal of Medicinal Chemistry, Journal Year: 2022, Volume and Issue: 235, P. 114303 - 114303

Published: March 18, 2022

Language: Английский

Citations

42

Visible-Light-Promoted Selective Sulfonylation and Selenylation of Dienes to Access Sulfonyl-/Seleno-benzazepine Derivatives DOI
Zhen Zhang,

Pengpeng Tan,

Shilong Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4208 - 4213

Published: May 30, 2023

A novel visible-light-promoted selective sulfonylation and selenylation of dienes with selenosulfonates has been developed. This technology provides mild access to a wide range sulfonyl benzo[b]azepinones seleno-benzo[b]azepines. Preliminary mechanistic studies suggest that the involves radical engaged cascade process, is accomplished through sequential oxidation/electrophilic cyclization process. The large-scale operation late-stage modification experiment reveal promising utility this protocol.

Language: Английский

Citations

38

Recent advances in the synthesis of organoselenium heterocycle conjugates DOI
Saad Shaaban,

Hussein Ba‐Ghazal,

Yasair S. Al‐Faiyz

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 157, P. 133957 - 133957

Published: March 23, 2024

Language: Английский

Citations

16

Recent Advances in Cyclization Reactions of 1,6‐Enynes DOI

J.H. Liu,

Sheng‐Qi Xu,

Yaping Han

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1220 - 1268

Published: Jan. 22, 2024

Abstract Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products biologically active pharmaceutical molecules. Over the past few decades, development versatile synthetic approaches via cascade cyclization reactions 1,6‐enynes for construction a series fused spiro compounds has been focus great deal research initiatives. These synthesis strategies peculiarly fascinating context assembly wide array molecules, products, agrochemicals, functional materials. In this review, recent developments transformations with diverse coupling reagents summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed 1,6‐enynes; 3) Metal‐free 4) Visible‐light‐induced 5) Electrocatalytic 1,6‐enynes.

Language: Английский

Citations

13

Visible Light-Induced Cascade Cyclization of 3-Aminoindazoles, Ynals, and Chalcogens: Access to Chalcogen-Containing Pyrimido[1,2-b]-indazoles DOI

Jinlei Zhou,

Wen Li,

Huitao Zheng

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(7), P. 2754 - 2759

Published: March 19, 2021

A direct cascade cyclization of 3-aminoindazoles, ynals, and accessible chalcogens facilitated by visible light has been developed. series fluoroactive selenium/tellurium-substituted pyrimido[1,2-b]-indazoles were easily accessed in moderate to good yields with a broad scope. Furthermore, we surveyed the spectral properties selenide prepared this method.

Language: Английский

Citations

54

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances DOI
Jamal Rafique, Daniel S. Rampon, Juliano B. Azeredo

et al.

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(10), P. 2739 - 2761

Published: March 3, 2021

Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well modern organic synthesis, attracting considerable attention from scientific community. Therefore, construction C-Se bond via facile, efficient sustainable strategies to access complex scaffolds simple substrates are appealing hot topic. Visible light can be regarded alternative source energy is associated environmentally-friendly processes. Recently, use visible-light mediated seleno-functionalization has emerged ideal powerful route obtain high-value selenylated products, diminished cost waste. This approach, involving photo-excited substrates/catalyst single-electron transfer (SET) between presence visible been successfully used versatile direct insertion organoselenium moieties activated unactivated C(sp3 )-H, C(sp2 C(sp)-H bonds C-heteroatom bonds. In most cases, ease operation accessibility (LEDs or commercial CFL bulbs) makes this approach more attractive than traditional strategies.

Language: Английский

Citations

44

Radical selenation of C(sp3)–H bonds to asymmetric selenides and mechanistic study DOI
Xin Wang,

Jia Lei,

Sa Guo

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(10), P. 1526 - 1529

Published: Jan. 1, 2022

Selenides are important structural motifs with a broad range of biological activities and versatile transformational abilities. In this study, novel mild method was developed for the facile synthesis asymmetric selenides under metal-free conditions. The key features reaction include good functional-group tolerance, use readily available reagents cheap, low-toxicity solvent, amenability to gram-scale synthesis. results preliminary radical-trapping experiments kinetic isotope effect study support radical process.

Language: Английский

Citations

39