Visible-light-mediated catalyst-free synthesis of trifluoromethyl(spiro)-epoxides bearing contiguous quaternary centers

Lin, Jingchuan; Zhang, Yu; Wang, Jinxin; Han, Xinyu; Zhu, Shenglan; Li, Tong; Zhu, Yanping; Zhang, Wei-Dong

doi:10.1039/d4qo00184b

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00184b

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Visible-light-mediated catalyst-free synthesis of trifluoromethyl(spiro)-epoxides bearing contiguous quaternary centers

Jingchuan Lin,

Yu Zhang,

Jinxin Wang

et al.

Abstract: Herein, we describe a non-covalent complex-mediated epoxidation strategy that can yield highly selective central spiro-epoxides by irradiation with visible light without the need for catalyst addition.

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Cited by 3 publications

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“…We are inspired by the light-induced generation of carbenes from diazo compounds and their transformations for C–C and C–heteroatom bond formation . The N -tosylhydrazones are readily available from aldehydes, ketones, and α-ketoesters, which have been underexplored for the generation of carbenes in the presence of light and a base . Our idea is to avoid ex situ-generated diazo compounds, which are explosive and have issues with regard to storage and stability.…”

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confidence: 99%

Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones

Yamini,

Babbar,

Yadagiri

2024

Org. Lett.

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Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report the light-driven intramolecular cyclopropanation of alkene-tethered N-tosylhydrazones in the presence of Cs 2 CO 3 and visible light. We have synthesized various electronically and sterically substituted and heterocyclic-containing fused-(spiro)cyclopropane γ-lactone compounds in good yields under transition metal-free conditions using a radical-free approach. In addition, the onepot synthesis of fused-cyclopropane γ-lactones from α-ketoesters and their synthetic utility are also presented.Letter pubs.acs.org/OrgLett

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confidence: 99%

Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones

Yamini,

Babbar,

Yadagiri

2024

Org. Lett.

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Light‐Induced Transformations of Donor‐Donor Diazo Compounds Derived from N‐Sulfonylhydrazones

Yamini,

Junaid,

Yadagiri

2024

Chemistry An Asian Journal

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The donor‐donor carbene chemistry field is underdeveloped and often relies on harsh reaction conditions, utilizing either thermal or oxidative process with or without transition‐metal catalysts. In this review, we discussed the synthesis and transformation of donor‐donor diazo compounds from N‐sulfonylhydrazones in the presence of light and base. The N‐sulfonylhydrazones are easily accessible from the corresponding carbonyl compounds and sulfonyl hydrazides through condensation. The in situ generated N‐sulfonyl anion in the presence of base would undergo the N‐S bond cleavage with the aid of light to generate the donor‐donor diazo compounds. The donor‐donor diazo compounds showed various reactivity in the presence of light for the C–C and C–X bond formation, cyclopropanation reactions, and synthesis of nitrogen, oxygen‐containing heterocyclic compounds, which all are discussed under metal‐free conditions.

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Access to Diverse Carbonyl Compounds by Catalyst‐Free and Photoinduced Aerobic Cleavage of C=N Bonds

Xia,

Wang,

et al. 2024

Chemistry A European J

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Functional group interconversion is of great significance in organic synthesis. However, aerobic cleavage of C=N bonds to access carbonyl compounds still suffered from some limitations such as harsh reaction conditions, stoichiometric oxidants, poor substrate scope and use of toxic reagents. Herein, we report a catalyst‐free and photo‐induced aerobic cleavage of C=N bonds to afford diverse carbonyl compounds using oxygen from air as green oxidant. This mild methodology permits N‐tosylhydrazones converted into the corresponding carbonyl compounds including ketones, aldehydes and carboxylic acids, showing broad functional group tolerance and compatibility. Moreover, the gram‐scale reaction and post‐modification of complicated molecules proved the applicability and efficiency of this strategy. Finally, a plausible mechanism was proposed based on spectroscopic investigations and detailed mechanistic studies.

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Visible-light-mediated catalyst-free synthesis of trifluoromethyl(spiro)-epoxides bearing contiguous quaternary centers

Abstract: Herein, we describe a non-covalent complex-mediated epoxidation strategy that can yield highly selective central spiro-epoxides by irradiation with visible light without the need for catalyst addition.

Cited by 3 publications

References 83 publications

Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones

Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones

Light‐Induced Transformations of Donor‐Donor Diazo Compounds Derived from N‐Sulfonylhydrazones

Access to Diverse Carbonyl Compounds by Catalyst‐Free and Photoinduced Aerobic Cleavage of C=N Bonds

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