Recent Advances in Cyclization Reactions of 1,6‐Enynes

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

---

Visible-Light-Mediated Three-Component Radical Iodosulfonylative Cyclization of Enynes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(13), P. 2515 - 2519

Published: March 30, 2022

An efficient three-component radical iodosulfonylative cyclization of enynes is described. The visible-light irradiation iodoform with sulfinates enables sulfonyl generation under catalyst- and oxidant-free conditions triggers the addition, iodination cascade reactions, giving various vinyl iodide containing sulfones in moderate to good yields.

Language: Английский

---

Recent Advances in Light-Induced Selenylation

ACS Organic & Inorganic Au, Journal Year: 2022, Volume and Issue: 2(6), P. 455 - 463

Published: Aug. 19, 2022

Selenium-containing organic molecules have recently found a plethora of applications, ranging from synthesis to pharmacology and material sciences. In view these concepts, the development mild, efficient, general protocols for formation C–Se bonds is desirable, light induced approaches are appealing ways. The aim this Review provide reader with most recent examples promoted selenylation processes.

Language: Английский

---

Selectfluor-Mediated Electrophilic Annulation of 2-Alkynyl Biaryls with Diorganyl Diselenides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 16790 - 16796

Published: Nov. 28, 2023

A general and efficient method for the synthesis of various selanyl phenanthrenes/polycyclic heteroaromatics through electrophilic annulation 2-alkynyl biaryls with diorganyl diselenides under metal-free mild conditions was established. The sulfanyl phenanthrene also obtained in moderate yields.

Language: Английский

---

Photo- or Electrochemical Cyclization of Dienes with Diselenides to Access Seleno-Benzo[b]azepines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7245 - 7255

Published: May 23, 2023

A cascade selenylation/cyclization of dienes with diselenides has been realized under visible-light irradiation or electrolysis conditions. Employing O2 electricity as a "green" oxidant, this protocol provides green and efficient method for an array biologically important seleno-benzo[b]azepine derivatives in moderate to good yields. The direct sunlight gram-scale reaction render the approach practical attractive.

Language: Английский

---

Visible‐Light‐Driven Cyclizations

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 635 - 697

Published: Jan. 13, 2024

Abstract In recent years, the interest to develop cyclizations promoted by visible light has been gaining a lot of attention due its sustainability aspect. this review, we summarize most important advances in period describing methods used generate different ring sizes, while focusing on mechanistic details these reactions.

Language: Английский

---

Stereo- and Regioselective cis-Hydrophosphorylation of 1,3-Enynes Enabled by the Visible-Light Irradiation of NiCl₂(PPh₃)₂

Organic Letters, Journal Year: 2021, Volume and Issue: 23(8), P. 2981 - 2987

Published: March 30, 2021

Described herein is a stereo- and regioselective cis-hydrophosphorylation reaction of the internal alkyne 1,3-enynes that accesses various 1,3-dienes in good isolated yields. The visible-light irradiation NiCl2(PPh3)2 allows generation highly reactive nickel(II)-phosphorus species subsequently migrate into protonate resulting vinyl nickel species, leading to phosphinoyl 1,3-butadienes under mild conditions.

Language: Английский

---

Recent applications of photoredox catalysis inO-heterocycles: A short review

Synthetic Communications, Journal Year: 2021, Volume and Issue: 51(20), P. 3033 - 3058

Published: Aug. 26, 2021

The oxygenated heterocycles are widely found in natural products, medicinal molecules, and various multifunctional components. A large number of synthetic methods have been reported indicating the synthesis potent biological activities these heterocycles. Visible light photocatalysis has evolved as a used method organic synthesis, which emerged relevant tool this area. This review summarizes recent advances made photocatalysed oxygen-containing heterocyclic compounds.

Language: Английский

---

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

ChemCatChem, Journal Year: 2022, Volume and Issue: 14(14)

Published: May 2, 2022

Abstract The 1, n ‐enynes are potent scaffolds in organic synthesis, providing a state‐of‐the‐art approach for synthesizing various acyclic and carbo‐ heterocyclic compounds. Radical cascade cyclization C−H functionalization of have gained immense attention the synthetic community. Significant advancement this field has been developed over years, employing harsh expensive metal catalysts usually associated with intense product purification unwanted side‐products. In context, advent visible light photocatalysis as mild efficient area is welcome step. Herein, we provide an exclusive overview recent developments light‐assisted manipulation ‐enynes. We classified review into 1,3‐, 1,4‐, 1,5‐, 1,6‐, 1,7‐, 1,8‐enynes, well dienyne, enediyne‐based reactions.

Language: Английский

---

Three-Component Radical Iodonitrosylative Cyclization of 1,6-Enynes under Metal-Free Conditions

Organic Letters, Journal Year: 2021, Volume and Issue: 23(13), P. 5044 - 5048

Published: June 10, 2021

A three-component, metal-free radical cascade iodonitrosylative cyclization reaction was described. The nitroso generated from tert-butyl nitrite and triggered the addition/cyclization/iodination/oxidation sequences. variety of 1,6-enynes were tested proved to be compatible, delivering various highly functionalized hetero- all-carbon cycles nitro vinyl C–I bonds containing pyrrolidines, tetrahydrofuran, cyclopentane in moderate excellent isolated yields.

Language: Английский

---