A Computational Study on the Photochemical O–H Functionalization of Alcohols with Diazoacetates DOI
Chao Pei, René M. Koenigs

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(10), P. 6832 - 6837

Published: May 2, 2022

In this computational study, we provide a detailed analysis of the underlying reaction mechanism and show that singlet carbene is initially formed. Depending on pKA alcohol, can engage in direct protonation or enol formation to yield O-H functionalization product. On contrary, propargylic alcohols take up dual role form complex with intermediate leads facile cyclopropenation reactions.

Language: Английский

Unlocking novel reaction pathways of diazoalkanes with visible light DOI
Claire Empel, Chao Pei, René M. Koenigs

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(17), P. 2788 - 2798

Published: Jan. 1, 2022

In this feature article, the photolysis and dye-sensitized reactions of diazoalkanes are discussed applications in organic synthesis presented.

Language: Английский

Citations

102

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

46

Additive-free synthesis of S-substituted isothioureas via visible-light-induced four-component reaction of α-diazoesters, aryl isothiocyanates, amines and cyclic ethers DOI

Yufen Lv,

Hongyu Ding,

Jinmao You

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 109107 - 109107

Published: Sept. 16, 2023

Language: Английский

Citations

46

Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate DOI Open Access
Bao‐Gui Cai, Jun Xuan

Chinese Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 41(12), P. 4565 - 4565

Published: Jan. 1, 2021

Carbene is one of the most important synthetic intermediates in organic synthesis.In past few decades, transition-metal catalyzed carbene transfer reactions have made remarkable development.Recently, visible light-promoted transformation diazo compounds through formation free as key intermediate begun to rise.The reaction only need light sole energy source which meets concept green chemistry.Since pioneering works developed by groups Diaves and Zhou, photo-promoted has attracted more attentions.On basis previous work, latest progress this field further improved, mainly focuses on recent new under irradiation contributions reported from Chinese research group.The future development direction, well challenges prospected.

Language: Английский

Citations

66

Photocatalyst-free visible-light-mediated three-component reaction of α-diazoesters, cyclic ethers and NaSCN to access organic thiocyanates DOI

Zhiwei Wang,

Na Meng,

Yufen Lv

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(2), P. 107599 - 107599

Published: June 13, 2022

Language: Английский

Citations

57

Direct benzylation reactions from benzyl halides enabled by transition-metal-free photocatalysis DOI

Panjie Xiang,

Kai Sun, Shuang Wang

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 33(12), P. 5074 - 5079

Published: March 26, 2022

Language: Английский

Citations

49

Visible-light-driven multicomponent reactions to access S-alkyl phosphorothioates using elemental sulfur as the sulfur source DOI

Chengming Qu,

Ruisheng Liu,

Zhiwei Wang

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(12), P. 4915 - 4920

Published: Jan. 1, 2022

A convenient and eco-friendly visible-light promoted multicomponent protocol has been developed for the synthesis of S -alkyl phosphorothioates by using elemental sulfur as cheap odorless source.

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‐Mediated Cyclopropanation: Recent Progress DOI

Ze‐Le Chen,

Yang Xie, Jun Xuan

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(44)

Published: Oct. 21, 2022

Abstract Cyclopropanes are one of the most important strained rings existing in various pharmaceutical products and secondary metabolites. They also widely used total synthesis natural products, medicinal chemistry, materials science. In past years, photochemical cyclopropanation has been gradually developed as a robust attractive synthetic method to prepare diverse cyclopropane backbones. this review, we summarize recent advances visible light‐mediated synthesis, especially using carbene transfer strategy photocatalytic radical reactions.

Language: Английский

Citations

39