Regioselective Disulfide-Catalyzed Photocatalytic Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

Fernandes, Rodney A.; Kumar, P. B. Sunil; Bhowmik, Amit; Gorve, Dnyaneshwar A

doi:10.1021/acs.orglett.2c00884

Cited by 11 publications

(10 citation statements)

References 57 publications

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“…Similar to the results obtained with the disulfides, 4-mercaptopyridine as well as other aryl and alkyl thiols proved to be unproductive. Recently, applications of 2-aldrithiol or 2-mercaptopyridine as catalysts have emerged in synthetic chemistry, exhibiting unique catalytic activities in both two electron and one electron manners different from common disulfides and thiols. Fontaine reported 2-mercaptopyridine-catalyzed transfer borylation of heteroarenes. , Stephenson developed photochemical intermolecular [4 + 2] and [3 + 2] cycloaddition catalyzed by 2-aldrithiol. , Fernandes employed 2-aldrithiol as a catalyst to generate sulfide radicals for promoting photocatalytic oxidative cleavage of 1-arylbutadienes .…”

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confidence: 78%

Deuterium- and Electron-Shuttling Catalysis for Deoxygenative Deuteration of Alcohols

He,

2023

Org. Lett.

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A practical and precise method for visible-light-promoted deoxygenative deuteration of common aliphatic alcohols using D2O as the deuterium source is reported. Upon intermediacy of xanthate anions, a variety of primary, secondary, and tertiary alcohols can be facilely transformed into deuterioalkanes with excellent D-incorporation at predicted sites. The deoxygenation and deuteration sequence is catalyzed by in situ formed deuterated 2-mercaptopyridine, which plays dual roles as a deuterium atom transfer catalyst and an electron shuttle as well.

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confidence: 78%

Deuterium- and Electron-Shuttling Catalysis for Deoxygenative Deuteration of Alcohols

He,

2023

Org. Lett.

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“…(E)-3-(4-Isopropylphenyl)acrylaldehyde (A5). 59,60 Obtained 110 mg in 32% yield; 1 H NMR (500 MHz, CDCl 3 ) δ 9.69 (d, J = 7.7 Hz, 1H), 7.50 (d, J = 8.1 Hz, 2H), 7.46 (d, J = 15.9 Hz, 1H), 7.29 (d, J = 8.1 Hz, 2H), 6.69 (dd, J 1 = 15.9 Hz, J 2 = 7.7 Hz, 1H), 3.00−2.89 (m, 1H), 1.27 (d, J = 6.9 Hz, 6H). 13 (E)-3-(6-Methoxypyridin-3-yl)acrylaldehyde (A8).…”

Section: ■ Conclusionmentioning

confidence: 99%

Structure-Guided Design, Synthesis, and Antivirulence Assessment of Covalent Staphylococcus aureus Sortase A Inhibitors

Yue,

Yuan,

et al. 2024

J. Med. Chem.

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Sortase A (SrtA) is a membrane-associated cysteine transpeptidase required for bacterial virulence regulation and anchors surface proteins to cell wall, thereby assisting biofilm formation. SrtA is targeted in antivirulence treatments against Gram-positive bacterial infections. However, the development of potent small-molecule SrtA inhibitors is constrained owing to the limited understanding of the mode of action of inhibitors in the SrtA binding pocket. Herein, we designed and synthesized a novel class of covalent SrtA inhibitors based on the binding mode detailed in the X-ray crystal structure of the ML346/Streptococcus pyogenes SrtA complex. ML346 analog Y40 exhibited 2-fold increased inhibitory activity on Staphylococcus aureus SrtA and showed superior inhibitory effects on biofilm formation in vitro. Y40 protected Galleria mellonella larvae fromS. aureusinfections in vivo while minimally attenuating staphylococcal growth in vitro. Our study indicates that the covalent SrtA inhibitor Y40 is an antivirulence agent that is effective againstS. aureusinfections.

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“…Additional references cited within the Supporting Information. [60][61][62][63][64][65][66][67][68][69][70] Author Contributions…”

Section: Supporting Informationmentioning

confidence: 99%

Multicomponent and Metal‐Free Diels–Alder/Aromatization Approach to the Stereospecific Synthesis of E‐(Hetero)Stilbenes and Diarylacetylenes

Ballarotto,

Cerra,

Temperini

2023

Eur J Org Chem

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Herein, we present a novel and metal‐free approach to the stereospecific synthesis of E‐stilbenes. Starting from substituted 6‐arylhexa‐3,5‐dien‐2‐ones, a multicomponent enolacetylation/intermolecular Diels–Alder reaction was performed using ethyl acetate as a green solvent. The obtained cycloadducts were then oxidized without purification to produce the stilbenic products in good yields up to 67 % and with complete (E)‐stereospecificity and regioselectivity. Moreover, heterostilbenes were synthetized using this approach, displaying the potential applications of this protocol in pharmaceutical and material sciences. The proposed methodology was further extended to the synthesis of diarylacetylenes, furnishing a new metal‐free synthetic access to this important class of compounds. Furthermore, DFT calculations were performed confirming a concerted [4+2] reaction mechanism of the key ring‐forming step. At last, the energetic analysis of the possible transition states helps to shed some light on the experimentally observed total regio‐ and chemoselectivity.

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Regioselective Disulfide-Catalyzed Photocatalytic Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

Cited by 11 publications

References 57 publications

Deuterium- and Electron-Shuttling Catalysis for Deoxygenative Deuteration of Alcohols

Deuterium- and Electron-Shuttling Catalysis for Deoxygenative Deuteration of Alcohols

Structure-Guided Design, Synthesis, and Antivirulence Assessment of Covalent Staphylococcus aureus Sortase A Inhibitors

Multicomponent and Metal‐Free Diels–Alder/Aromatization Approach to the Stereospecific Synthesis of E‐(Hetero)Stilbenes and Diarylacetylenes

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