Synthesis of Indolizines via Tf 2 O-Mediated Cascade Reaction of Pyridyl-enaminones with Thiophenols/Thioalcohols

Self Cite

A highly efficient and regioselective method for constructing functionalized conjugated enals via the Tf 2 O-mediated tandem reaction of enaminones with thiophenols has been described. Chain products with excellent stereoselectivity could be obtained through substrate regulation. Additionally, a feasible method for synthesizing β-naphthalaldehydes through PhSO 2 Na/ DABCO promoting hydrogen atom transfer process has also been reported here. Mechanism studies have shown that 2-formyl vinyl triflate 8 and sulfonylated enal 9 were the key intermediates in this process.

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tf₂O-Mediated Tandem Reaction of Enaminones for the Synthesis of Functionalized Conjugated-Enals/β-Naphthalaldehydes

Zhang,

Lin,

Wang

et al. 2023

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“…Accordingly, considerable efforts have been devoted to the synthesis of these heterocyclic motifs . The intramolecular or intermolecular cyclization of pyridine and its derivatives is the most commonly used approach . Besides, the annulation of substituted pyrroles with alkenes or alkynes also provides a practical strategy to access indolizine scaffolds .…”

Section: Introductionmentioning

confidence: 99%

Switchable Synthesis of Spirodihydroindolizines and Indolizines from Aurones and Pyridin-2-yl Active Methylene Compounds

Liu,

Wang,

et al. 2024

A novel and flexible domino reaction of aurones with pyridin-2-yl active methylene compounds promoted by I 2 /BF 3 has been developed to afford spirodihydroindolizines and indolizines in a controllable manner. When the reaction was performed in 1,2-dichloroethane at 80 °C, a variety of spirodihydroindolizines were obtained, whereas it almost exclusively provided a series of indolizines when the reaction was performed in a mixed solvent of 1,2-dichloroethane and N,Ndimethylformamide at a relatively higher temperature of 100 °C. Being metal-free, excellent product selectivity, high atom economy, good functional group tolerance, and feasibility for large-scale synthesis are the salient features of the developed methodology.

“…It is widely used in the fields of chemistry, pesticides, and pharmaceutical chemistry; has some biological activity in the field of medicine; − and also has some application value in the field of materials science. − Furthermore, the O–O bond of the peroxide structure can be found on many reactants. Under the influence of heat, transition metal catalysts, or radiation, the relatively weak O–O bond is cleaved, allowing further synthesis of alcohols, aldehydes, ketones, and other substances. − The bifunctional groups of olefins can rapidly form C–S bonds to synthesize alkyl/arylthiocompounds. − The synthesis methods of peroxides are very diverse, and the bifunctionalization of olefins is often used to synthesize peroxides; some cheap metals are often used as catalysts for reactions. For example, copper can be used as a reaction catalyst to synthesize the target product of peroxides in the strategy using olefins, tert -butyl hydroperoxide (TBHP), and nucleophilic reagents as reactants. ,− Fe is also one of the commonly used catalysts for the synthesis of peroxides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α/β-Aromatic Peroxy Thiols Mediated by Iodine Source

Zhang,

Liu,

Abdukerem

et al. 2024

Peroxygenated compounds have wide applications in various fields, including chemistry, pharmaceutical chemistry, medicine, and materials science. However, there is still a need for more efficient and environmentally friendly synthesis methods for such compounds. Herein, we investigated the two-step, one-pot, regioselective synthesis of α/β-aromatic peroxy thiols. We explored various substrates and solvents for the reaction and identified the optimal reaction conditions. We successfully obtained several peroxy thiols in moderate to good yields via the selective generation of effective intermediates of iodoalkyl peroxides at room temperature without the need for metal catalysts.