[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives DOI

Shanliang Dong,

Xiang Fu, Xinfang Xu

et al.

Asian Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 9(8), P. 1133 - 1143

Published: June 16, 2020

Abstract Pyridinium ylide is a versatile building block in synthetic organic chemistry, especially the synthesis of N ‐heterocycles. In this minireview, we have summarized advances [3+2]‐cycloaddition catalytically generated pyridinium for indolizines (since 1970s). Accordingly, discussed article situ from carbene precursors and ‐heteroarenes under catalytic conditions, including photocatalysis/thermocatalysis, metal‐catalysis. The metal‐catalyzed version main focus, which classified based on type dipolarophiles, alkyne alkene, each class further subdivided according to metal catalysts used these reactions. analogous vinyl with pyridines, formation other or different ‐heteroarenes, been also included herein separately.

Language: Английский

Blue light-promoted photolysis of aryldiazoacetates DOI Creative Commons
Igor D. Jurberg, Huw M. L. Davies

Chemical Science, Journal Year: 2018, Volume and Issue: 9(22), P. 5112 - 5118

Published: Jan. 1, 2018

Aryldiazoacetates can undergo photolysis under blue light irradiation (460–490 nm) at room temperature and air in the presence of numerous trapping agents, such as styrene, carboxylic acids, amines, alkanes arenes, thus providing a straighforward general platform for their mild functionalization.

Language: Английский

Citations

337
Recent progress on donor and donor–donor carbenes DOI

Dong Zhu,

Lianfen Chen,

Hanlin Fan

et al.

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 49(3), P. 908 - 950

Published: Jan. 1, 2020

This review highlights the recent advances in donor and donor–donor carbenes.

Language: Английский

Citations

335
Synthesis and Transformations of Nitrones for Organic Synthesis DOI
Shun‐Ichi Murahashi, Yasushi Imada

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(7), P. 4684 - 4716

Published: March 15, 2019

Nitrones are important compounds and highly useful in many aspects. The first part describes the methods for synthesis of nitrones, which environmentally friendly. Catalytic oxidations, condensations, other reactions described. nitrones thus obtained key intermediates biologically nitrogen compounds. second fundamental transformations will provide strategies means construction with nucleophiles or radicals, C–H functionalization, various addition last particularly selective carbon—carbon bond formations. 1,3-Dipolar cycloaddition excluded because size review is limited excellent reviews have been published Chemical Reviews.

Language: Английский

Citations

236
C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions DOI
R. Vicente

Chemical Reviews, Journal Year: 2020, Volume and Issue: 121(1), P. 162 - 226

Published: July 8, 2020

This review highlights key reactivities relying on C–C bond cleavages of cyclopropenes. Metal-catalyzed and metal-free transformations are covered in reactions involving direct ring-opening processes or through nonisolable cyclopropane intermediates generated from Special emphasis is the synthetic utility mechanistic aspects methodologies discussed along revision. Different types separate sections including generation vinyl carbenes their reactions, metathesis processes, heterocycles syntheses, SEAr metalation-ring opening sequences, cycloadditions ring-cleavages rearrangements. The focus results described 2007 to end 2019, yet relevant pioneering eventually included.

Language: Английский

Citations

155
Selective [2σ + 2σ] Cycloaddition Enabled by Boronyl Radical Catalysis: Synthesis of Highly Substituted Bicyclo[3.1.1]heptanes DOI

Tao Yu,

Jinbo Yang, Zhijun Wang

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(7), P. 4304 - 4310

Published: Feb. 10, 2023

In contrast to the traditional and widely-used cycloaddition reactions involving at least a π bond component, [2σ + 2σ] radical between bicyclo[1.1.0]butanes (BCBs) cyclopropyl ketones has been developed provide modular, concise, atom-economical synthetic route substituted bicyclo[3.1.1]heptane (BCH) derivatives that are 3D bioisosteres of benzenes core skeleton number terpene natural products. The reaction was catalyzed by combination simple tetraalkoxydiboron(4) compound B2pin2 3-pentyl isonicotinate. broad substrate scope demonstrated synthesizing series new highly functionalized BCHs with up six substituents on 99% isolated yield. Computational mechanistic investigations supported pyridine-assisted boronyl catalytic cycle.

Language: Английский

Citations

123
Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI
Ziyan Zhang, Vladimir Gevorgyan

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

Citations

59
Application of (4+3) cycloaddition strategies in the synthesis of natural products DOI
Zengsheng Yin, Yun He, Pauline Chiu

et al.

Chemical Society Reviews, Journal Year: 2018, Volume and Issue: 47(23), P. 8881 - 8924

Published: Jan. 1, 2018

This review summarizes the applications of (4+3) cycloadditions, both classical and formal, in syntheses natural products last two decades.

Language: Английский

Citations

126
Silver-catalyzed decarboxylative radical cascade cyclization toward benzimidazo[2,1-a]isoquinolin-6(5H)-ones DOI
Kai Sun, Shijun Li, Xiaolan Chen

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(19), P. 2861 - 2864

Published: Jan. 1, 2019

A simple and efficient decarboxylative radical addition/cyclization strategy was developed, by which a wide range of benzimidazo[2,1-a]isoquinoline-6(5H)-ones were prepared in one-pot via reaction functionalized 2-arylbenzoimidazoles carboxylic acids the presence K2S2O8/AgNO3 under mild conditions.

Language: Английский

Citations

124
Sulfoxonium ylides: simple compounds with chameleonic reactivity DOI
Giorgiana Denisa Bisag, Silvia Ruggieri, Mariafrancesca Fochi

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(43), P. 8793 - 8809

Published: Jan. 1, 2020

Sulfur ylides first disclosed in 1930 started to gain more attention the 1960s, thanks mainly studies by Corey and Chaykovsky on their use for preparation of strained rings. More recently, chemistry these compounds has experienced important growth, part due similarity reactivities with diazo compounds. This short review provides an overview great assortment reactions sulfoxonium ylides, outlining a comparison between congeners: sulfonium Insertion reactions, cyclisation ring-opening are highlighted, giving particular catalytic asymmetric methodologies.

Language: Английский

Citations

115
(3+3)‐Annulation of Carbonyl Ylides with Donor–Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis DOI

Martin Petzold,

Peter G. Jones,

Daniel B. Werz

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(19), P. 6225 - 6229

Published: Feb. 13, 2019

The first (3+3)-annulation process of donor-acceptor cyclopropanes using synergistic catalysis is reported. Rh2 (OAc)4 -catalyzed decomposition diazo carbonyl compounds generated ylides in situ. These 1,3-dipoles were converted with cyclopropanes, activated by Lewis acid catalysis, to afford multiply substituted pyran scaffolds high yield and diastereoselectivity. Extensive optimization studies enabled access 9-oxabicyclo[3.3.1]nonan-2-one 10-oxabicyclo[4.3.1]decen-2-ol cores, exploiting solvent effects on intermediate reactivity.

Language: Английский

Citations

101