Csp3–H Imination Using Arylazo Sulfone as a N Source: An Approach to Access Imines DOI
Yulei Zhao, Shuai Li, Yuhang Fan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(31), P. 5911 - 5915

Published: Aug. 2, 2023

An unprecedented Csp3-H imination reaction using arylazo sulfones as the readily accessible and stable N source is reported. The synthetic virtues are demonstrated through mild conditions, simple operation, good air compatibility, functional group tolerance, well suitability for gram-scale reaction. resulting imines can be further converted to α-amino acids. presented results shed light on an unusual usage of will inspire novel experimental design by source.

Language: Английский

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
Visible light-mediated photolysis of organic molecules: the case study of diazo compounds DOI
Rafael D. C. Gallo, Guilherme Cariello Silva, Tales A. C. Goulart

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(48), P. 7346 - 7360

Published: Jan. 1, 2023

This article discusses the photochemistry of several diazo compounds undergoing visible light-mediated photolysis to generate free carbenes (or other highly reactive intermediates), which can be sequentially trapped by different reacting partners.

Language: Английский

Citations

45
Visible-Light-Mediated Formal Carbene Insertion Reaction: Enantioselective Synthesis of 1,4-Dicarbonyl Compounds Containing All-Carbon Quaternary Stereocenter DOI
Hua Zhang,

Zheyuan Wang,

Zirui Wang

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(9), P. 5510 - 5516

Published: April 25, 2022

We developed an efficient visible-light-mediated formal carbene insertion reaction of 1,3-diketones with diazoesters for the construction enantioenriched 1,4-dicarbonyl compounds a quaternary carbon center. Combining visible light and Brønsted acid catalyst, chiral were achieved in good yields high enantioselectivities by photochemical transfer protocol.

Language: Английский

Citations

43
Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates DOI Creative Commons

Daksh Singh Davas,

Dinesh Kumar Gopalakrishnan,

Sandeep Kumar

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(3), P. 1073 - 1080

Published: March 1, 2024

Herein, we report a highly regioselective [4 + 2]-annulation of vinyl sulfoxonium ylides with ynoates under light-mediated conditions. The reaction proceeds through the new dienyl ylide, which undergoes photolysis blue light irradiation to give substituted naphthalene scaffolds. method presented here operates at room temperature and does not require addition an external photosensitizer. in situ-generated ylide absorbs acts as photosensitizer for formation arenes. synthetic potential these benzannulations was further illustrated by various transformations scale-up reaction. Moreover, control experiments quantum chemical calculations reveal mechanistic details developed

Language: Английский

Citations

9
Multiprobe Photoproximity Labeling of the EGFR Interactome in Glioblastoma Using Red-Light DOI
Feifei Tong, Weidong Zhou, Michalina Janiszewska

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Photocatalytic proximity labeling has emerged as a valuable technique for studying interactions between biomolecules in cellular context, providing precise spatiotemporal control over protein labeling. One significant advantage of these methods is their modularity, allowing the use single photocatalyst with different reactive probes to expand interactome coverage and capture diverse interactions. Despite advances, fewer have been developed using red-light excitation, limiting photoproximity more complex media such tissues animal models. Herein, we develop platform under utilizing catalyst two distinct probe types. We first design carbene based system that utilizes sulfonium diazo probes. This successfully applied on A549 cells epidermal growth factor receptor (EGFR) Cetuximab-Chlorin e6 conjugate. Benchmarking against established techniques indicates this approach performs comparably leading carbene-based methods. Next, leverage strong singlet oxygen generation (SOG) ability Chlorin establish an alternative aniline hydrazide EGFR directed chemoproteomics experiments reveal overlap system, capturing subset identified by SOG system. Finally, deploy our characterization resected human glioblastoma (GBM) tissue samples removed from locations same tumor, representing tumor's infiltrating edge its viable center, identifying several GBM specific interacting proteins may serve launch point future therapeutic campaigns.

Language: Английский

Citations

1
Visible-light-induced organocatalytic enantioselective N–H insertion of α-diazoesters enabled by indirect free carbene capture DOI Creative Commons
Wengang Guo, Ying Zhou,

Hongling Xie

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 14(4), P. 843 - 848

Published: Nov. 29, 2022

While asymmetric insertion of metal carbenes into H-X (X = C, N, O, etc.) bonds has been well-established, control over free is challenging due to the presence strong background reactions and lack any anchor for a catalyst interaction. Here we have achieved first photo-induced metal-free bond this type. With visible light used as promoter chiral phosphoric acid catalyst, α-diazoesters aryl amines underwent smooth N-H form enantioenriched α-aminoesters with high efficiency good enantioselectivity under mild conditions. Key success was use DMSO an additive, which served rapidly capture highly reactive carbene intermediate domesticated sulfoxonium ylide.

Language: Английский

Citations

38
Dark and Light Reactions of Carbenes─Merging Carbene Transfer Reactions with N-Heterocyclic Carbene Catalysis for the Synthesis of Hydroxamic Acid Esters DOI
Bao‐Gui Cai, Qian Li, Claire Empel

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(18), P. 11129 - 11136

Published: Aug. 30, 2022

Herein, we report visible light and N-heterocyclic carbene (NHC) jointly promoted multicomponent transfer reactions. Under the optimized reaction conditions, two kinds of important hydroxamic acid esters were obtained in good yields depending on media used. The key to this success was driven by blue light-promoted generation free species fast situ formation under NHC-catalyzed conditions. mild excellent functional group tolerance, useful synthetic transformations, successful modification natural products drug molecules proved utility practicality method.

Language: Английский

Citations

29
Photochemical multicomponent transformation of acceptor-only diazoalkanes by merging their cycloaddition and carbene reactivities DOI
Bao‐Gui Cai, Guoyong Xu, Jun Xuan

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(9), P. 108335 - 108335

Published: March 15, 2023

Language: Английский

Citations

13
Visible-Light-Induced Imide Synthesis through a Nitrile Ylide Formation/Trapping Cascade DOI
Bao‐Gui Cai,

Wei‐Zhong Yao,

Lei Li

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(36), P. 6647 - 6652

Published: Sept. 2, 2022

A visible-light-promoted three component reaction of diazo compounds, nitriles, and carboxylic acids is reported. The utilizes acceptor-only compounds as carbene precursors nitriles carbene-trapping reagents to form the key nitrile ylides. Under optimal conditions, a wide range imide products were obtained in good excellent yields. gram-scale synthesis synthetic application isoquinoline-1,3(2H,4H)-dione derivatives further proved value this method.

Language: Английский

Citations

20
Photochemical Reactions of Sulfur Ylides DOI
Radell Echemendía,

Kauê C. Capellaro,

Antonio C. B. Burtoloso

et al.

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(13), P. 978 - 990

Published: May 6, 2024

Abstract: Photochemical reactions offer unparalleled opportunities to access elusive chemical pathways and develop innovative strategies for constructing complex molecules. Within organic synthesis, photochemical have become indispensable tools accessing molecular structures, such as pharmaceuticals natural products. The ability of sulfur ylides participate in these diverse processes has made them the synthetic chemist's toolbox. use transformations garnered significant attention chemistry community, they serve powerful intermediates several transformations. This review article presents a comprehensive overview mediated by ylides. Herein, we describe key aspects reactivity presence light. compounds can be classified into three categories: energy acceptors, electron donors, trapping reagents.

Language: Английский

Citations

4