Radical Carbocyclization Intercepted Reductive C‐C Bond Formation Between 1,n‐Enynes or Dienes and Electron‐Poor Olefins/Alkynes DOI

Subhadeep Hazra,

Manveer Patel, Jaideep Saha

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4688 - 4693

Published: Aug. 20, 2024

Abstract Metal hydride catalyzed hydrogen atom transfer (MHAT) reaction of 1,6‐enyne and electron‐poor alkene progresses through a radical cascade, involving ene‐yne cyclization exocyclic C−C bond formation superseding the direct reductive olefin cross‐coupling; which is realized in current study. The generality this manifold demonstrated with range functionalized dienes structurally distinct olefins alkynes as partners. Current work unveils merger MHAT‐based olefin‐hydro functionalization ene‐one cyclization.

Language: Английский

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

Photocatalytic Sulfonylation: Innovations and Applications DOI
Anxiang Huang,

Rui Li,

Qi‐Yan Lv

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Language: Английский

Citations

10

Radical cascade cyclization of 1,n-enynes under photo/electrochemical conditions DOI

Zhenzhi Cai,

Sven Trienes, Kairui Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5735 - 5745

Published: Jan. 1, 2023

During the past decade, photo- and electrochemical reactions proceeding via single-electron-transfer (SET) triggered radical pathways have emerged as an indispensable strategy for efficient formation of chemical bonds.

Language: Английский

Citations

20

Visible‐Light‐Driven Cyclizations DOI Creative Commons
Emilia Oueis, Mirella Elkadi, Ramón Rios

et al.

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

Citations

7

Time and Atom Economical Regio‐ and Chemoselective Radical Cyclization of Unactivated 1,6‐Enynes Under Metal‐ and Oxidant‐Free Conditions DOI
Mohana Reddy Mutra, Jing Li,

Yu‐Ting Chen

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 28(42)

Published: May 19, 2022

We developed time-atom economic regio- and chemoselective sulfonyl radical triggered 5-exo-dig cyclization of unactivated 1,6-enynes with halides under metal, additive-free reaction conditions to achieve highly substituted five-membered heterocyclic compounds. This transformation creates three new bonds, such as C-SO2 , C-C, active C-I/Br bonds. Importantly, one-pot protocols produce desired products directly from sodium sulfinates have an additional advantage minimising chemical waste, saving time, simplifying practical aspects compared existing protocols.

Language: Английский

Citations

23

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

Citations

15

Metal‐Free Visible‐light Mediated C−S Bond Formation DOI
Ashish Kumar Sahoo,

Dinabandhu Barik,

Binoyargha Dam

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: June 26, 2023

Abstract The upsurge in interest the development of methodologies for synthesis sulfur‐containing compounds via use visible‐light has been established as a sustainable tool organic chemistry. Particularly, mediated C−S bond formation gained popularity due to its operational simplicity, minimized by‐products, easy handling, mild reaction conditions, etc. Photochemistry not only provides way synthesize complex molecules but also ability overcome many challenges which are difficult attain by conventional thermal pathways. Owing biological importance compounds, present review focused on under metal‐free conditions visible‐light. objective current is bring out unearthing collection regarding photoredox catalysis. For better understanding, categorized according mode reactions viz , difunctionalization alkenes and alkynes, C−H functionalization, radical cyclization. All each sections described with selected examples proper explanation proposed mechanism.

Language: Английский

Citations

15

Difunctionalization of Dienes, Enynes and Related Compounds via Sequential Radical Addition and Cyclization Reactions DOI Creative Commons
Sanjun Zhi,

Hongjun Yao,

Wei Zhang

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(3), P. 1145 - 1145

Published: Jan. 23, 2023

Radical reactions are powerful in creating carbon–carbon and carbon–heteroatom bonds. Designing one-pot radical with cascade transformations to assemble the cyclic skeletons two new functional groups is both synthetically operationally efficient. Summarized this paper recent development of involving addition cyclization dienes, diynes, enynes, as well arene-bridged arene-terminated compounds for preparation difunctionalization compounds. Reactions carried out initiators, transition metal-catalysis, photoredox, electrochemical conditions included.

Language: Английский

Citations

12

Electrosynthesis of bridged or fused sulfonamides through complex radical cascade reactions: divergence in medium-sized ring formation DOI Creative Commons
Yan Zhang,

Zhenzhi Cai,

Chunhang Zhao

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(13), P. 3541 - 3547

Published: Jan. 1, 2023

Radical cascade addition is one of the most important and efficient strategies for synthesis valuable heterocycles with structural diversity complexity.

Language: Английский

Citations

11

Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides DOI

Shengkun Guo,

Xiaoyu Shen, Xiaoyun Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 15969 - 15974

Published: Oct. 30, 2023

Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation diselenides, triggering addition with 1,3-dienes to form allyl intermediate. Subsequent rapid Z/E isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization various nucleophiles.

Language: Английский

Citations

11