Visible-Light-Mediated Strategies for the Preparation of Oxime Ethers Derived from O–H Insertions of Oximes into Aryldiazoacetates DOI
Mateus L. Stivanin, M.T. Duarte, Luiz Paulo Melchior de Oliveira Leão

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 17528 - 17532

Published: Nov. 18, 2021

Two visible-light-mediated O–H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct takes place. THF, there is additional incorporation of ring-opened form this into structure product. These metal-free mild tolerant air moisture. The preparation an acaricide has been developed as example synthetic application.

Language: Английский

Recent progress and perspectives in photo-induced organic reactions of acylsilanes DOI

Wan Pyo Hong,

Hee Nam Lim, Inji Shin

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(3), P. 819 - 836

Published: Jan. 1, 2023

This review provides recent advances and insights into photoirradiation reactions of acylsilanes, notably via key nucleophilic siloxycarbene intermediates. Nucleophilic addition, insertion reaction, cyclization are discussed in terms reaction mechanism scope.

Language: Английский

Citations

38

Oxygen-doped carbon nitride for enhanced photocatalytic activity in visible-light-induced decarboxylative annulation reactions DOI

Anzai Shi,

Kai Sun,

Yanxuan Wu

et al.

Journal of Catalysis, Journal Year: 2022, Volume and Issue: 415, P. 28 - 36

Published: Sept. 29, 2022

Language: Английский

Citations

37

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

Chemoselective Synthesis of Unsymmetrical Dithioacetals through Sequential Carbene Insertion and Acetal Exchange of Acylsilanes and Thiols under Visible Light Irradiation DOI
Wang Zhang, Danni Yang,

Dou-Dou Guo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1282 - 1286

Published: Feb. 1, 2024

Dithioacetals are a frequently used motif in synthetic organic chemistry, and most existing reports discuss only symmetrical dithioacetals. Examples of unsymmetrical dithioacetals scarce, few general methods for the selective synthesis these compounds exists. An intriguing visible-light-induced strategy has been established this work sequential reactions S–H insertion acetal exchange between acylsilanes two different thiols that deliver wide variety moderate yields. The were obtained with high selectivity, great functional groups tolerated.

Language: Английский

Citations

6

A visible light-mediated three-component strategy based on the ring-opening of cyclic ethers with aryldiazoacetates and nucleophiles DOI
Mateus L. Stivanin, Rafael D. C. Gallo, João Paulo M. Spadeto

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(5), P. 1321 - 1326

Published: Jan. 1, 2022

A visible light-mediated strategy insensitive to air or moisture allows a 3-component reaction between aryldiazoacetates, cyclic ethers and various nucleophiles afford formal O–H inserted products of more complex alcohols.

Language: Английский

Citations

28

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

28

Chemodivergent Synthesis of Oxazoles and Oxime Ethers Initiated by Selective C–N/C–O Formation of Oximes and Diazo Esters DOI
Zhenjie Qi, Shaozhong Wang

Organic Letters, Journal Year: 2021, Volume and Issue: 23(21), P. 8549 - 8553

Published: Oct. 7, 2021

Chemodivergent reactions of oximes and diazo esters involving Rh-catalyzed [3+2] annulation photodriven O-H insertion have been developed to generate oxazoles oxime ethers. A range aldehyde ketone reacted with α-diazocarbonyl compounds in a controllable manner which functional groups, including ketone, ester, amide, ether, thiol silane, alkene, allene, alkyne were well tolerated.

Language: Английский

Citations

32

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