Visible-Light-Induced Three-Component Reactions of α-Diazoesters, Indazoles and Cyclic Ethers DOI

Wei Wang,

Yan Liu, Yang Fu

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3889 - 3902

Published: Oct. 29, 2024

Abstract An efficient method was developed for the construction of N-short-chain ether-attached carbonyl group-substituted indazoles. The visible-light-induced three-component reactions α-diazoesters, indazoles, and cyclic ethers, under extremely mild conditions, led to corresponding mixture N 1 2 short-chain ether-substituted indazoles in good excellent yields.

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

56
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 photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

Citations

11
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
Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors DOI Open Access
Yang Xie, Jun Xuan

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(12), P. 4247 - 4247

Published: Jan. 1, 2022

Language: Английский

Citations

21
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
Visible-Light-Induced Carbene Insertion into P–H Bonds between Acylsilanes and H-Phosphorus Oxides DOI
Xiaoyu Mo, Yuexiang Xie,

Lin‐Li Wei

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2338 - 2343

Published: March 28, 2023

An intriguing visible-light-induced strategy has been established for the P-H insertion reaction between acylsilanes and H-phosphorus oxides that, upon a subsequent acidic process, deliver wide variety of α-hydroxyphosphorus in good yields (up to 93% yield). The metal-free protocol represents unique example C-P bond formation through situ generation siloxycarbenes. This methodology features advantages operational simplicity, mild conditions, broad substrate scope, column free gram-scale synthesis.

Language: Английский

Citations

12
Visible-Light-Driven gem-Difluorocyclopropanation of gem-Difluoroalkenes with Diazo Compounds DOI

Xinxin Han,

Xin Liu, Christophe Len

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134653 - 134653

Published: April 1, 2025

Language: Английский

Citations

0
Sequential In Situ-Formed Kukhtin–Ramirez Adduct and P(NMe2)3-Catalyzed O-Phosphination of α-Dicarbonyls with P(O)–H DOI
Yuan‐Yuan Huang, Nan Wang, Zheng‐Guang Wu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7595 - 7600

Published: Oct. 13, 2023

O-Phosphination of α-dicarbonyls via sequential in situ formation a Kukhtin-Ramirez adduct and P(NMe2)3-catalyzed process has been exploited for the synthesis α-phosphoryloxy carbonyls. A range P(O)-H derivatives, including diarylphosphine oxides, arylphosphinates, phosphinates, are competent candidates to be introduced into this transformation, various carbonyls obtained. This approach possesses advantages mild conditions, simple operations, atom economy, high efficiency, gram-scale synthesis, which make it promising toolbox.

Language: Английский

Citations

9
Photocatalyzed Aerobic Cross-Dehydrogenative Coupling of Diarylphosphine Oxides with Alcohols and Phenols DOI
Hongyan Zhou,

Chengqi Wu,

Yating Han

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2435 - 2439

Published: March 19, 2024

A photocatalytic cross-dehydrogenative coupling of diarylphosphine oxides with alcohols and phenols has been developed. Using organic dye Rose Bengal as the photocatalyst air oxidant, reaction proceeded smoothly at room temperature. Both were feasible, affording various organophosphinates in high yields. The absence a halogenating reagent, transition-metal catalyst, green mild conditions make this strategy environmentally benign sustainable. Mechanistic studies indicated that is enabled by cooperation photoredox catalysis photosensitization.

Language: Английский

Citations

3