Ketone Skeletal Modification via a Metallaphotoredox-Catalyzed Deacylation and Acylation Strategy DOI

Ke‐Han He,

Na Jin, J. Paul Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9503 - 9507

Published: Oct. 28, 2024

Herein, we describe a dual catalytic strategy that employs dihydroquinazolinones, derived from ketone analogs, as versatile intermediates for acylation via α C–C cleavage with 2-pyridyl esters, facilitating the efficient synthesis of variety ketones. The reaction accommodates wide range ketones and carboxylic acids, showing tolerance to various functional groups. versatility this synthetic technique is further highlighted through its application in late-stage modification pharmaceuticals biologically active natural products.

Language: Английский

Photocatalytic Bilateral Disulfuration of Thioethers Toward α‐Sulfide Disulfides With Antibacterial Activity DOI Creative Commons

Qingqiang Tian,

Chuxia Wang,

Bingrui Liu

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: April 26, 2025

Abstract α −Sulfide disulfides represent valuable motifs in organic and pharmaceutical chemistry. However, the limited availability of synthetic approaches for −sulfide has impeded progress this field. In study, a photocatalytic approach to synthesizing modifiable is presented using accessible sulfides bilateral disulfurating reagent. The reaction proceeds under mild conditions demonstrates broad substrate compatibility, accommodating both aromatic aliphatic sulfides. Moreover, synthesized display robust reactivity subsequent transformations with different electrophiles. Notably, protocol can also be applied modification polymer matrices. Bioassays further reveal that certain target compounds exhibit significant antibacterial activity against plant pathogens, such as Xanthomonas oryzae pv. ( Xoo ), pathovar oryzicola Xoc Dickeya zeae D. ).

Language: Английский

Citations

0

Organo-Photoredox Catalyzed gem-Difluoroallylation of Ketone-Derived Dihydroquinazolinones with α-Trifluoromethyl Alkenes via C(sp3)-C Bond and C(sp3)-F Bond Cleavage DOI
Yue Zhang,

Tianshuai Zhu,

Yuqian Lin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(27), P. 5561 - 5568

Published: Jan. 1, 2024

An organo-photoredox catalyzed defluorinative alkylation of ketone-derived dihydroquinazolinones with α-trifluoromethyl alkenes is described, providing a facile access to diverse set gem -difluoroalkenes.

Language: Английский

Citations

3

Rich electron delocalization structure in carbon nitride inducing radical transfer for high‐performance photocatalytic uranyl reduction DOI Creative Commons
Zhangmeng Liu, Yayao Li, Shuaiqi Yao

et al.

Carbon Energy, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 23, 2024

Abstract Investigating the activation of persulfate process through heterogeneous carbonaceous catalysts to expedite reduction uranyl ions (U(VI)) is imperative. The primary hurdle involves understanding transfer and distribution photogenerated carriers during in this intricate system deciphering role activated groups promoting efficiency. In study, we strategically regulate structure polymeric carbon nitride promote N‐doped state, thereby facilitating delocalization electron enrichment. resulting active sites effectively activate peroxyl disulfate (PDS), generating radicals that selective U(VI). This strategic approach mitigates inherent disadvantage short half‐life free persulfate‐based advanced oxidation processes. As a consequence our endeavors with simultaneous presence PDS hydrogen peroxide, achieve an exceptional photoreduction efficiency 100% within remarkably period 20 min. breakthrough presents high‐efficiency application significant potential for addressing pollution associated uranyl‐containing wastewater. Our findings not only contribute fundamental AOPs but also offer practical solution implications environmental remediation.

Language: Английский

Citations

3

Oxysulfonylation of Alkynes with Sodium Sulfinates to Access β-Keto Sulfones Catalyzed by BF3·OEt2 DOI Creative Commons

Shi‐Wei Yu,

Zu-Jia Chen,

Huanqing Li

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3559 - 3559

Published: July 28, 2024

An efficient and operationally simple method for the synthesis of β-keto sulfones through BF

Language: Английский

Citations

2

Construction of C—S and C—Se Bonds from Unstrained Ketone Precursors under Photoredox Catalysis DOI Open Access
Xinyu Liu, Shun‐Yi Wang

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(4), P. 1382 - 1382

Published: Jan. 1, 2024

Language: Английский

Citations

0

Visible Light‐mediated Late‐stage Thioetherification of Mercaptopurine Derivatives DOI
Yuhua Ge,

Yijiang Peng,

Ruoqian Xie

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(48)

Published: June 26, 2024

We disclose herein a novel and general radical approach to alkylthiopurines, encompassing 4 types of thiopurines, as well their corresponding ribosides. This strategy is achieved through visible light-mediated late-stage functionalization the sulfur atoms mercaptopurines. The in situ-generated disulfide was proposed pivotal neutral intermediate for this transformation. present photo-mediated homolytic C-S bond formation preparation alkylthiopurines alkylthiopurine nucleosides. Despite presence reactive sites Minisci reaction, chemoselective S-alkylation remained predominant pathway. method allows introduction broad spectrum alkyl groups onto atom unprotective mercaptopurine derivatives, 2-, 6-, 8-mercaptopurine rings. Organoborons serve efficient eco-friendly alkylating reagents, providing advantages terms readily availability, stability, reduced toxicity. Further derivatization thioetherified nucleosides, together with anti-tumor assays, led discovery potent agents an IC

Language: Английский

Citations

0

Na2CO3-Promoted Synthesis of Thiocarbamates from Isocyanates and Thiols under Mild Conditions DOI

Yingbin Gong,

Leilei Yan,

Zhiqiang Guo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6277 - 6281

Published: Jan. 1, 2024

A method for the synthesis of thiocarbamates catalyzed by Na 2 CO 3 from isocyanates and thiols was developed, possible mechanism proposed. This has advantages high yield, good tolerance, atom economy mild conditions.

Language: Английский

Citations

0

Direct excitation strategy for deacylative couplings of ketones DOI
Jianbin Li,

Ding Zhang,

Lida Tan

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(42)

Published: July 24, 2024

Abstract The homolysis of chemical bonds represents one the most fundamental reactivities excited molecules. Historically, it has been exploited to generate radicals under ultraviolet (UV) light irradiation. However, unlike contemporary radical‐generating mechanisms, direct excitation homolyze and produce aliphatic carbon‐centered visible remains rare, especially in metallaphotoredox cross couplings. Herein, we present our design dihydropyrimidoquinolinone (DHPQ) reagents derived from ketones, which can undergo formal deacylation homolytic C−C bond cleavage release alkyl without external photocatalysts. Spectroscopic computational analysis reveal unique optical structural features DHPQs, rationalizing their faster kinetics radical generation than a structurally similar but visible‐light transparent precursor. Such capability allows DHPQ facilitate wide range Ni‐metallaphotoredox couplings with aryl, alkynyl acyl halides. Other catalytic non‐catalyzed alkylative transformations DHPQs are also feasible various acceptors. We believe this work would be broad interest, aiding synthetic planning simplified operation expanding reach photocatalyst‐free approaches cutting‐edge research.

Language: Английский

Citations

0

Deuteration Degree Controllable Synthesis of Aryl Deuteromethyl Ethers Through Dual photoredox and Thiol Catalysis DOI
Junjie Yang, Zhongxian Li,

Zhihui Huang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(62)

Published: Aug. 22, 2024

Herein, we report a facile and efficient deuteration degree controllable method for the preparation of aryl deuteromethyl ethers through dual photoredox thiol catalysis using phenols as starting materials inexpensive D

Language: Английский

Citations

0

Thioesterification and Hydrothiolation of α, β‐Unsaturated Esters with Aliphatic Thiols under Mild Conditions DOI
Yijun Shi,

Guoli YAN,

Shuo Yin

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(39)

Published: Oct. 1, 2024

Abstract Herein the one‐pot thioesterification and hydrothiolation of α , β ‐unsaturated esters with aliphatic thiols was reported at room temperature. The mechanism indirectly revealed which thioester intermediate. advantages this method included transition‐metal‐free, mild conditions, broad substrate scope good functional group tolerance. On other hand, temperature also developed.

Language: Английский

Citations

0