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

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

12

External electrolyte-free electrochemical one-pot cascade synthesis of 4-thiocyanato-1H-pyrazoles DOI

Wei-Bao He,

Sai-Jie Zhao,

Jingyang Chen

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(2), P. 107640 - 107640

Published: June 30, 2022

Language: Английский

Citations

34

Metal-free visible-light-induced multi-component reactions of α-diazoesters leading to S-alkyl dithiocarbamates DOI

Yufen Lv,

Ruisheng Liu,

Hongyu Ding

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(13), P. 3486 - 3492

Published: Jan. 1, 2022

A metal-free and visible-light-promoted strategy has been developed for the synthesis of S -alkyl dithiocarbamates through multicomponent reactions α-diazoesters, amines CS 2 .

Language: Английский

Citations

29

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 Intermolecular Cyclopropanation Reactions of Allylic Alcohols for the Synthesis of [3.1.0]-Bicyclohexanes DOI
Chao Pei, Claire Empel, René M. Koenigs

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(1), P. 169 - 173

Published: Jan. 5, 2023

Cyclopropane-fused lactones are highly desirable in drug and natural products synthesis. Herein, we report on a photochemical, chemoselective reaction of aryldiazoacetates with allylic alcohols that furnishes cyclopropane-fused lactone skeletons efficiently one step. The diastereoselectivity the protocol was precisely controlled, cyclopropanation via free carbene intermediate followed by transesterification constitutes series bicyclic high yield without formation ether byproducts typical O–H insertion reactions.

Language: Английский

Citations

17

Emerging progress: photochemical transformation of nitroso compounds DOI

Ze‐Le Chen,

Qiangqiang Li, Armido Studer

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 17, 2024

Language: Английский

Citations

7

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

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

Recent Advances in the Synthesis of Di- and Trisubstituted Hydroxylamines DOI Creative Commons
Jarvis Hill, Thomas D. Beckler, David Crich

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2816 - 2816

Published: March 21, 2023

As an underrepresented functional group in bioorganic and medicinal chemistry, the hydroxylamine unit has historically received little attention from synthetic community. Recent developments, however, suggest that hydroxylamines may have broader applications such a review covering recent developments synthesis of this is timely. With mind, primarily covers past 15 years preparation di- trisubstituted hydroxylamines. The mechanism reactions key features shortcomings are discussed throughout review.

Language: Английский

Citations

10