Visible light driven amide synthesis in water at room temperature from Thioacid and amine using CdS nanoparticles as heterogeneous Photocatalyst

Das, Sudipto; Ray, Shounak; Ghosh, Abhisek Brata; Samanta, Partha; Samanta, Suvendu; Adhikary, Bibhutosh; Biswas, Papu

doi:10.1002/aoc.4199

Cited by 23 publications

(14 citation statements)

References 92 publications

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“…Photocatalytic synthesis of amide by CdS had been realized in water at room temperature under 30 W CFL lamp irradiation, giving 73-97 % yields of amides (Scheme 6b). [28] Surprisingly, the procedure can even take place in relatively moderate sunlight irradiation and a gram scale reaction was performed with a yield of 88 % under standard conditions. It has been reported that metal sulfides can facilitate the formation of CÀ C bonds as a photocatalyst.…”

Section: Binary and Ternary Metal Sulfidesmentioning

confidence: 99%

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

2019

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metal sulfides belong to an important subgroup of semiconductor photocatalysts that could promote a variety of valuable redox reactions under mild conditions. One notable merit of metal sulfides is their relatively smaller bandgaps than metal oxides, which in turn make sure that many of them can directly utilize visible light. Historically, the deployment of metal sulfides for visible-light-induced organic transformations took place shortly after the genesis of the research field of heterogeneous photocatalysis. In this review, we primarily focus on recent state-of-the-art advancements of metal sulfide photocatalysis aimed at visible-light-induced selective organic transformations. Interests in this specific branch of photocatalysis have been rekindled due to the new methods for materials synthesis; the pursuit of new mechanisms; or the integration of metal sulfides with metal oxides, metal nanoparticles or other emerging materials. Thus we categorize them into four sections according to the different strategies in developing novel or more efficient organic processes. Binary and ternary metal sulfides, usually associated with new materials synthesis and mechanistic insights, can be used directly for visible-lightinduced organic transformations. This is the basis of other further developments and will be introduced firstly. Next, the cooperation between metal sulfides and metal oxides or metal nanoparticles can be conducive to many photocatalytic systems. These developments will be discussed in the next two ensuing sections. Furthermore, the integration of metal sulfides with recent developed emerging materials such as metalorganic frameworks (MOFs), graphene and graphitic carbon nitride (g-C 3 N 4 ) will be discussed in another section to highlight the importance of merging metal sulfides with these materials. We attempt to keep an impartial panorama of these four distinctive sections even though the phases of development are quite different among sections, leaving plenty of room for the future expansion of this burgeoning area.

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Section: Binary and Ternary Metal Sulfidesmentioning

confidence: 99%

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

2019

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“…Finally, on the basis of the above control experiments and previous reports, plausible mechanisms are proposed for the formation of amide bonds by spontaneous and electrosynthetic reactions. In the process of spontaneous reaction (Scheme ), the ionization equilibrium of thiobenzoic acid ( 1 ) in EtOAc results in the presence of thiobenzoate anion ( 1‐A ) and a proton.…”

Section: Figurementioning

confidence: 53%

“…The resultso ft hese control experiments indicate that the formation of disulfide intermediates is criticalf or both spontaneous and electrosynthetic reactions. Finally,o nt he basis of the above controle xperiments and previousr eports, [12,13] plausible mechanismsa re proposed for the formation of amide bonds by spontaneous and electrosynthetic reactions. In the process of spontaneous reaction (Scheme 6), the ionization equilibrium of thiobenzoic acid (1) in EtOAc resultsi nt he presence of thiobenzoate anion (1-A) and ap roton.…”

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confidence: 72%

“…One is that thioacids react with some chemical reagents such as Sanger reagents & Mukaiyama reagents, organoisonitriles, Cu II reagents, carbon disulfide, organonitrite, and nanocatalysts to form more reactive thio‐intermediates, which can react with amines to give the amides (Scheme a). The other one is that thioacids can be converted to disulfides, which can be nucleophilically substituted by amines to form the corresponding amides . Methods for converting thioacids to disulfides have been reported by several research groups: Mali and Gopi used I 2 as a mediator to form disulfides, Tan and co‐workers developed a photo‐oxidation process with Ru(bpy) 3 Cl 2 as a photocatalyst to obtain disulfides from potassium thioacids, and Biswas and co‐workers reported that CdS nanoparticles can act as a heterogeneous photocatalyst to catalyze the formation of disulfides form thioacids (Scheme b).…”

Section: Figurementioning

confidence: 99%

“…The other one is that thioacids can be converted to disulfides, which can be nucleophilically substituted by amines to form the corresponding amides. [11][12][13] Methods for converting thioacids to disulfides have been reported by several research groups:M ali and Gopi used I 2 as am ediator to form disulfides, [11] Tana nd co-workersd eveloped ap hoto-oxidation process with Ru-(bpy) 3 Cl 2 as ap hotocatalystt oo btain disulfides from potassium thioacids, [12] and Biswas and co-workers reported that CdS nanoparticles can act as ah eterogeneous photocatalyst to catalyze the formation of disulfides form thioacids [13] (Scheme1b). Although these reported strategies are effective, they have some drawbacks, such as the use of toxic reagents, metals,o r expensive catalysts.…”

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confidence: 99%

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Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis

et al. 2019

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Amide bond formation is one of the most important basic reactions in chemistry. A catalyst‐free approach for constructing amide bonds from thiocarboxylic acids and amines was developed. The mechanistic studies showed that the disulfide was the key intermediate for this amide synthesis. Thiobenzoic acids could be automatically oxidized to disulfides in air, thioaliphatic acids could be electro‐oxidized to disulfides, and the resulting disulfides reacted with amines to give the corresponding amides. By this method, various amides could be easily synthesized in excellent yields without using any catalyst or activator. The successful synthesis of bioactive compounds also highlights the synthetic utility of this strategy in medicinal chemistry.

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Visible‐Light‐Mediated Amide Synthesis in Deep Eutectic Solvents

et al. 2023

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In the present study, for the first time environmentally friendly deep eutectic solvents (DESs) are used as reaction media to perform an efficient, simple and straightforward photocatalytic amide synthesis at room temperature using thioacids and amines. This method features mild conditions, a broad substrate scope, high yields (≤99%) under ambient conditions with air and moisture tolerance. Moreover, the applied operationally mild reaction conditions tolerate the presence of several different functional group substituents on the amine counterpart. Finally, the developed approach allows the recycling of the reaction medium and catalyst for at least three consecutive cycles without a significant decrease in the reaction yield.

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Visible light driven amide synthesis in water at room temperature from Thioacid and amine using CdS nanoparticles as heterogeneous Photocatalyst

Cited by 23 publications

References 92 publications

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis

Visible‐Light‐Mediated Amide Synthesis in Deep Eutectic Solvents

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