Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones DOI
Pokhriyal Yamini, Akanksha Babbar, Dongari Yadagiri

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 6035 - 6040

Published: July 10, 2024

Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report light-driven intramolecular cyclopropanation alkene-tethered

Language: Английский

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
Oxime Ether Synthesis through O–H Functionalization of Oximes with Diazo Esters under Blue LED Irradiation DOI
Qian Li, Bao‐Gui Cai, Lei Li

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(17), P. 6951 - 6955

Published: Aug. 12, 2021

A green and sustainable oxime ether formation method via the visible-light-promoted O–H functionalization of oximes with diazo esters is described. The reaction occurs under very mild conditions (catalyst- additive-free) a high yield functional group tolerance. When was performed cyclic as solvent (e.g., THF, 1,4-dioxane, tetrahydropyran, ect.), an interesting photochemical three-component product obtained in good yields.

Language: Английский

Citations

62
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-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

39
Synthesis of trisubstituted hydroxylamines by a visible light-promoted multicomponent reaction DOI
Bao‐Gui Cai, Qian Li, Qiong Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(21), P. 5982 - 5987

Published: Jan. 1, 2021

A green and efficient route for the synthesis of trisubstituted hydroxylamines from β-keto ester, 2-nitrosopyridine aryldiazoacetates has been reported. This multicomponent reaction occurred under mild conditions without catalysts or additives.

Language: Английский

Citations

42
Enabling Cyclopropanation Reactions of Imidazole Heterocycles via Chemoselective Photochemical Carbene Transfer Reactions of NHC-Boranes DOI

Ze‐Le Chen,

Claire Empel, Kun Wang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(11), P. 2232 - 2237

Published: March 11, 2022

Herein we report a site-selective cyclopropanation of N-heterocyclic carbene (NHC)-borane complexes via photochemical transfer reactions. By subtle changes to the reaction conditions, this approach can be further extended toward difunctionalization NHC-boranes and B-H insertion reaction. Further investigations in continuous-flow applications synthetic transformations proved utility method. Theoretical calculations control experiments were performed explain observed selectivity.

Language: Английский

Citations

37
Recent advances in the application of ylide-like species in [4 + 1]-annulation reactions: an updated review DOI
Pavel Yu. Ushakov, Sema L. Ioffe, Alexey Yu. Sukhorukov

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(19), P. 5358 - 5382

Published: Jan. 1, 2022

In this review, the advances made over last 6 years in [4 + 1]-annulation reactions involving sulfonium, sulfoxonium and ammonium ylides, as well diazo compounds carbenes are summarized.

Language: Английский

Citations

34
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