Access to diverse carbonyl compounds by catalyst‐free and photoinduced aerobic cleavage of C=N bonds DOI

Dingding Xia,

Weijie Wang,

Xi‐Ke Xu

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 31, 2024

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

Language: Английский

A visible-light-promoted metal-free approach for N–H insertions by using donor/donor diazo precursors DOI Creative Commons
Yu Zhang, Qiannan Li, Ping Wang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4600 - 4608

Published: Jan. 1, 2024

A metal-free and catalyst-free strategy is reported to achieve N–H insertions by coupling N -tosylhydrazones with diverse amines including aminopyridines, anilines, aliphatic amines, other nucleophiles such as imidazoles indoles.

Language: Английский

Citations

10

Visible-Light-Mediated Three-Component Strategy for the Synthesis of Isoxazolines and Isoxazoles DOI
Yanchuan Li, Yu Zhang, Jinxin Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3130 - 3134

Published: April 8, 2024

Isoxazolines and isoxazoles commonly serve as core structures of many therapeutic agents natural products. However, the metal-free catalysis-free strategy for synthesis these privileged motifs at room temperature remains a challenging task. Herein, we report three-component to afford diverse isoxazolines via [3 + 2] cycloadditions in situ-formed nitronates olefins/alkynes under visible-light irradiation.

Language: Английский

Citations

8

Light-induced arylation (alkylation) of N-sulfonylhydrazones with boronic acids DOI

Mohammad Junaid,

Sharma Happy,

Dongari Yadagiri

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(20), P. 2796 - 2799

Published: Jan. 1, 2024

We report light-induced arylation (alkylation) for the synthesis of diarylmethanes, bis(diarylmethyl)benzenes, arylalkylmethanes, and triarylmethanes from readily accessible N -sulfonylhydrazones aryl/alkylboronic acids with aid Cs 2 CO 3 .

Language: Английский

Citations

6

Visible-light-induced decarboxylative cascade cyclization of acryloylbenzamides with N-hydroxyphthalimide esters via EDA complexes DOI
Qing Li, Zhi‐Qiang Zhu,

Wenyi Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(5), P. 965 - 969

Published: Jan. 1, 2024

A visible-light-induced, electron donor–acceptor (EDA) complex-enabled decarboxylative cascade reaction of acryloylbenzamides with alkyl N -hydroxyphthalimide esters by NaI/PPh 3 catalysis was developed.

Language: Английский

Citations

5

Synthesis of substituted benzylboronates by light promoted homologation of boronic acids with N-sulfonylhydrazones DOI Creative Commons
Álvaro Valdés-Maqueda, Lucía López, Manuel Plaza

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(47), P. 13765 - 13775

Published: Jan. 1, 2023

The homologation of boronic acids with diazoalkanes obtained by photochemical decomposition N -tosylhydrazones leads to substituted benzylboronates, previously unavailable under thermal conditions. Batch and continuous flow reactions are described.

Language: Английский

Citations

12

Facile Access to Hindered Ethers via Photoinduced O–H Bond Insertions DOI Creative Commons
Yu Zhang, Xinyu Han,

Dong Li

et al.

ACS Central Science, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Language: Английский

Citations

0

Catalytic π–π Interactions Triggered Photoinduced Synthesis of Biaryls DOI
Vishal Jyoti Roy,

Janardan Chakraborty,

Sudipta Raha Roy

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 3, 2024

A highly regioselective photocatalytic method to access a variety of biaryl motifs under metal-free conditions has been developed. The organophotocatalyst is involved in π–π stacking interactions with the alkyne species, which promotes this process thiophene. Mechanistic studies have shed light on these and overall process. Along broad functional-group tolerance excellent regioselectivity, protocol utilized late-stage functionalization pharmaceuticals other natural products.

Language: Английский

Citations

3

Photoinduced [3+2] Cycloaddition of Alkyl–Acceptor Diazoalkanes: Diversity-Oriented Synthesis of Pyrazolines Containing a Quaternary Center DOI

Fengya He,

Ziyi Sun,

Yiwei Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4031 - 4036

Published: Jan. 26, 2024

We present a new [3+2] cycloaddition reaction between alkyl-acceptor diazoalkanes under visible light irradiation. By employing easily accessible alkyl-acceptor-type or their precursor hydrazones as both 1,3-dipoles and dipolarophiles, diverse range of pyrazoline derivatives featuring quaternary center have been efficiently synthesized in predictable manner, with excellent functional group tolerance good yields. Furthermore, scale-up experiments downstream transformations the product were also detailed.

Language: Английский

Citations

2

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

Jingchuan Lin,

Yu Zhang, Jinxin Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3080 - 3088

Published: Jan. 1, 2024

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.

Language: Английский

Citations

2

Visible-light-induced [3+3] cycloaddition reaction of phenol and hydrazone to access 1,3,4-oxadiazines scaffolds DOI
Xuebin Qiao, Han Yu,

Sijun Huang

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 561, P. 114156 - 114156

Published: April 23, 2024

Language: Английский

Citations

2