C-S Cross-Coupling Reaction Using a Recyclable Palladium Prolinate Catalyst under Mild and Green Conditions

Santos, Beatriz F. dos; Silva, Caren D. G. da; Ramesh, K.; Oliveira, Aline R. de; Kupfer, Vicente L.; Rinaldi, Andrelson W.; Domingues, Nélson

doi:10.1002/slct.201701816

Cited by 12 publications

(21 citation statements)

References 26 publications

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“…In other words, we concluded that the increase of catalyst amount has accelerated the disulfide synthesis instead of the C‐S cross‐coupling reaction due to the presence of air (open flask) . Besides, to the best of our knowledge, thiol can also reduce the NOX of the metal, and the reduced metal species have an important role in the cross‐coupling reactions (CMD‐like process) . Thus, increasing the thiol loading allows us to produce the product in moderate yields (entry 4).…”

Section: Resultsmentioning

confidence: 92%

“…Later, we selected the reaction between 5‐bromo‐2,1,3‐benzothiadiazole ( 1 ) and thiophenol ( 2 ) as a standard reaction aiming to get all the reactional parameters needed for this reaction (optimization) (Table ). First of all, the reaction was performed under the same conditions already described by Domingues et al . for the C‐S cross‐coupling reaction (Entry 1) affording only moderate yield (53%) in EtOH.…”

Section: Resultsmentioning

confidence: 99%

“…Besides, the presence of thiolate and air oxygen produces a radical RS· that reacts to producing disulfide. In this sense, Domingues et al . have proved that disulfide is not suitable to perform this type of reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, aiming to perform an arylthiol functionalization at position 5, using a low‐cost, and effective methodology, herein we present a palladium‐catalyzed C‐S cross‐coupling methodology (Figure c). Our research group has already described some protocols using hybrid catalysts in some reactions, among them the C‐S cross‐coupling reaction using a recyclable Pd( L ‐Pro) 2 as catalyst under mild reaction conditions, and as Pd( L ‐Pro) 2 afforded high yields, and recyclability in those procedures, we decided to use it as the catalyst and describe a new, simple, and efficient methodology for C‐5 functionalization of BTD unit.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Efficient palladium‐catalyzed C‐S cross‐coupling reaction of benzo‐2,1,3‐thiadiazole at C‐5‐position: A potential class of AChE inhibitors

Santos

Pereira

Pinz

et al. 2020

Applied Organom Chemis

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Functionalization of 2,1,3‐benzothiadiazole (BTD) with thiols at C‐5 position remains low explored. Moreover, the arylthiol‐substitutions at this position are also unexplored and can not be found by a SN2 or SN1 reaction. In this sense, herein we present a new palladium‐catalyzed methodology for a wide variety of unpublished 5‐arylsulfanyl‐benzo‐2,1,3‐thiadiazole derivatives synthesis with moderate to high yields using a low catalytic loading of Pd(L‐Pro)2 as low‐coast, and efficient catalyst in low reaction time. Besides, we concluded that the pKa of thiol species has an important role in this catalysis, mainly in the CMD like catalytic cyclo process, which strongly interferes in the reaction yields. Furthermore, arylsulfanyl‐benzo‐2,1,3‐thiadiazoles derivatives have been assessed (in vitro) as potential acetylcholinesterase inhibitors.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Efficient palladium‐catalyzed C‐S cross‐coupling reaction of benzo‐2,1,3‐thiadiazole at C‐5‐position: A potential class of AChE inhibitors

Santos

Pereira

Pinz

et al. 2020

Applied Organom Chemis

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“…With this goal, our group has been investigating crosscoupling reactions, and we have previously described protocols for C-S cross-coupling by using a heterogeneous palladium catalyst. 16,17 As a continuation of this research, we herein introduce synthetic talc as an efficient, inexpensive, and eco-friendly heterogeneous support for immobilized palladium catalyst synthesis -LACOB-Pd1 and LACOB-Pd4. The difference between these two catalysts lies in the labels 1 and 4 which refer to the initial loading of the palladium salt added to synthetic talc (see the Supporting Information).…”

Section: Paper Synthesismentioning

confidence: 99%

Anchored Pd(0) Nanoparticles on Synthetic Talc for the Synthesis of Biaryls and a Precursor of Angiotensin II Inhibitors

et al. 2020

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The palladium-catalyzed Suzuki–Miyaura cross-coupling reaction is one of the most important and efficient reactions to prepare a variety of organic compounds, including biaryls. Despite the overwhelming number of reports related to this topic, some methodological difficulties persist in terms of catalyst handling, recovery, and reuse, as well as the reaction media. This work reports the rational design of new, efficient, cost-effective, and reusable palladium catalysts supported on synthetic talc for the Suzuki–Miyaura reaction. From the results, key points were identified: both designed catalysts accelerated the reaction in EtOH and an open-flask setup, affording moderate to excellent yields within a short time (e.g., 30 min) even for deactivated aryl halides; the protocol can be applied to a great number of both cross-coupling partners, showing an excellent functional group tolerance; the catalysts can be recovered and reused without significant loss of activity. This protocol was used for the synthesis of a precursor of angiotensin II inhibitors such as valsartan, losartan, irbesartan, and telmisartan.

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Mechanistic insights for nickel catalyzed light‐assisted carbon–sulfur cross‐coupling reaction

Silva

Santos

Domingues

2023

Applied Organom Chemis

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The C-S cross-coupling reaction is a very efficient and powerful tool for constructing C-S bonds. Despite the well-reported C-S cross-coupling protocols using aryl halides, this reaction using sp2-hybridized nonaromatic halides is still challenging. Herein, we report light-assisted C-S cross-coupling between thiols and 5-chlorobenzofurazan under blue LED irradiation. We used a new nickel catalyst to synthesize 11 unpublished compounds. Furthermore, we assessed the mechanism and the influence of light irradiation on this reaction and proposed a plausible mechanism that is mediated by the excited state of the nickel catalyst promoted by irradiation with blue light and the C-S coupling product formed. Notably, C-S cross-coupling under light irradiation was performed for the first time using a nickel catalyst in the absence of an external photocatalyst. We demonstrated that because nickel has a low energy barrier for oxidative addition, this protocol proceeded efficiently using chlorine as a leaving group, and the excited state of the nickel catalyst promoted reductive elimination with a lower energy barrier. It is important to mention that the procedure was tolerated by many functional groups within the thiol, affording a greater than 99% yield after reacting for 6 h.

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C-S Cross-Coupling Reaction Using a Recyclable Palladium Prolinate Catalyst under Mild and Green Conditions

Cited by 12 publications

References 26 publications

Efficient palladium‐catalyzed C‐S cross‐coupling reaction of benzo‐2,1,3‐thiadiazole at C‐5‐position: A potential class of AChE inhibitors

Efficient palladium‐catalyzed C‐S cross‐coupling reaction of benzo‐2,1,3‐thiadiazole at C‐5‐position: A potential class of AChE inhibitors

Anchored Pd(0) Nanoparticles on Synthetic Talc for the Synthesis of Biaryls and a Precursor of Angiotensin II Inhibitors

Mechanistic insights for nickel catalyzed light‐assisted carbon–sulfur cross‐coupling reaction

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