RESUMO
Allyl sulfones are an essential pharmacophore in many bioactive compounds. To combat their synthetic barrier, we report a practical, straightforward organophotocatalyzed methodology for accessing miscellaneously functionalized allyl sulfone derivatives using inexpensive and bench-stable sodium sulfinate salts under mild conditions. This photo-catalyzed radical sulfonylation provides access to a variety of allyl sulfones in good to excellent yields with high E : Z selectivity. A wide range of vinyl cyclopropanes, as well as aryl/hetero and alkyl sodium sulfinates, were tolerated and reliable in gram-scale synthesis. Later on, further functionalization of allyl sulfones was demonstrated. A plausible mechanism for radical sulfonylation is proposed from the control experiments.
RESUMO
This paper presents a green and efficient aqueous-phase method for the synthesis of thiosulfonates, which has the benefits of no need for catalysts or redox reagents and a short reaction time, providing a method with great economic value for synthesizing thiosulfonates. Furthermore, 3-Sulfenylindoles can be easily synthesized using this method, which expands the potential applications of this reaction.
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An efficient cross-coupling of aryl bromides with sodium sulfinates, using an organoboron photocatalyst with nickel, is described herein. Under the irradiation of white light, this dually catalytic system enables the synthesis of a series of sulfone compounds in moderate to good yields. A broad range of functional groups and heteroaromatic compounds is tolerated under these reaction conditions. The use of an organoboron photocatalyst highlights a sustainable alternative to iridium or ruthenium complexes. These findings contribute to the field of photochemistry and provide a greener approach to sulfone synthesis.
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An efficient and operationally simple method for the synthesis of ß-keto sulfones through the BF3·OEt2-promoted reaction of alkynes and sodium sulfinates is developed. With its facile and selective access to the targets, it features good functional group compatibility, mild conditions, easily available starting materials, and good yields. Notably, the reaction does not require metal catalysts or chemical reagents with pungent odors.
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The subject of this investigation is a new method for the construction of sulfonylated heterocycles which overcomes the limitations of classical approaches using a cheap feedstock sulfonylating agent, especially under photocatalyst- and metal-free conditions.
Assuntos
Alcinos , Sódio , CiclizaçãoRESUMO
Sulfonamides have a special role on medicine due to their broad biological activities, as bacterial infections, diabetes mellitus, oedema, hypertension prevention and treatment. In addition, sulfonamides are also useful in herbicides and pesticides. Herein, we communicate an efficient strategy for the preparation of sulfonamides via NH4 I-mediated amination of sodium sulfinates. This new method provides a general and environmentally friendly access to sulfonamide compounds and tolerates a wide range of functional groups.
Assuntos
Aminas , Sulfonamidas , Aminação , Estrutura Molecular , Sódio , SulfanilamidaRESUMO
A copper-catalyzed 8-aminoquinoline-directed oxidative cross-coupling of the C-H bond of ferrocene with sodium arylsulfinates has been achieved. The robust copper catalyst tolerates a range of methyl, tert-butyl, bromo, chloro, iodo and nitro functional groups in the phenyl ring, and set the stage for the synthesis of substituted ferrocene sulfones. Furthermore, X-ray crystal structure study on several ferrocenyl sulfones reveals the tetrahedral geometry around sulfur; interestingly, the O-S-O angle is larger than the electropositive substituent C-S-C angle which could be explained by Bent's rule. Further, unusual intramolecular O(S)â â â N(amide) short contacts (2.925-3) and O(S)â â â C=O were also noticed in ferrocenyl sulfones.
RESUMO
A copper-catalysed sulfenylation of indoles with sodium sulfinates that affords 3-sulfenylindoles in good-to-excellent yields in N,N-dimethyl formamide (DMF) is described. In the process, DMF serves not only as a solvent but also as a reductant. This transformation is easy to carry out and has mild reaction conditions and good functional group tolerance.