Methods for the direct synthesis of thioesters from aldehydes: a focus review

Jabarullah, Noor H.; Jermsittiparsert, Kittisak; Melnikov, Pavel; Maseleno, Andino; Hosseinian, Akram; Vessally, Esmail

doi:10.1080/17415993.2019.1658764

Cited by 34 publications

(12 citation statements)

References 67 publications

(60 reference statements)

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“…Because thioesters are mandatory intermediates in several key processes related with ATP usage and regeneration, they are even considered as possible precursors of life . Consequently, numerous methodologies for their preparation and further synthetic transformation have been developed . However, new and sustainable procedures are still in demand as alternatives.…”

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confidence: 99%

Palladium-Catalyzed Thiocarbonylation of Alkenes toward Linear Thioesters

Zhao

Geng

et al. 2021

ACS Catal.

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Thiocarbonylation of alkenes offers an ideal procedure for the synthesis of thioesters. However, thiocarbonylation of alkenes, especially styrenes, to produce valuable linear thioesters has remained a challenge. In this Letter, a general palladium-catalyzed thiocarbonylation of alkenes to produce linear thioesters has been achieved. Moderate to good yields of desired thioesters can be produced from readily available alkenes in a straightforward manner.

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confidence: 99%

Palladium-Catalyzed Thiocarbonylation of Alkenes toward Linear Thioesters

Zhao

Geng

et al. 2021

ACS Catal.

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“…The reason for this condition is unknown. However, in this aldehyde, OH-TEMPO might have promoted the reaction of NAC with CA because OH-TEMPO could catalyze the reaction …”

Section: Discussionmentioning

confidence: 99%

Cause Clarification of Cysteine Oxidation by Active Species Generated during the Oxidation Process of Cinnamaldehyde and Impact on an In Chemico Alternative Method for Skin Sensitization Using a Nucleophilic Reagent Containing Cysteine

Fujita

Yamamoto

Watanabe

et al. 2021

Chem. Res. Toxicol.

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Aldehydes comprise a major portion of skin sensitizers because they can react with both cysteine and lysine. Moreover, cinnamaldehyde (CA) is a typical moderate sensitizer and is often used in an alternative test method for skin sensitization. The amino acid derivative reactivity assay (ADRA) is an in chemico test method that evaluates the reactivity of cysteine derivatives (N-(2-(1naphthyl)acetyl)-L-cysteine, NAC) and lysine derivatives with the test chemicals and uses CA as a proficiency substance. We found that NAC depletion for CA was only 10−20% when CA was used directly from the reagent bottle, although it increased to almost 100% when stored after being aliquoted from the reagent bottle. It was also found that this was due to the air oxidation of NAC itself rather than the reaction of NAC with CA, indicating that this result simply shows an increase in apparent reactivity. Aldehydes are known to produce active species, such as radicals, during air oxidation. Therefore, we investigated whether radicals were generated under storage conditions using the radical scavenger OH-TEMPO. LC/MS/MS analysis revealed that CA and OH-TEMPO complexes were produced during the air oxidation of CA. In the results of five aldehydes, similar to CA, active species were not generated as significantly as CA. Collectively, during the evaluation of the aldehydes, it can be seen that careful measures need to be taken to prevent the aldehydes from oxidizing during storage, indicating that assessment without preventing air oxidation carries an increased risk of overestimation compared with the intrinsic skin sensitization potency.

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“…As another class of carbonyl-containing substances, aldehydes also play important roles in the formation of thioesters. [45] In fact, aldehydes offer an excellent atom-economically sustainable alternative to other acylating agents due to their commercial availability, stability, low cost, and low toxicity. [46] Zhu and co-workers [47] developed a thioesterification reaction catalyzed by tetraethylammonium bromide (Scheme 21).…”

Section: Synthesis Of Thioesters From Aldehydesmentioning

confidence: 99%

A Recent Progress for the Synthesis of Thiocarboxylates

Wang

Dong

2022

Eur J Org Chem

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As a common and integral feature of many natural products, thiocarboxylates play an important role in biologically or pharmaceutically active compounds. Thiocarboxylates often show unique physiological activities in biology and drugs, which inspires many new therapeutic drugs. The related research and developments in thioester-based medicinal chemistry have been a rapidly developing and increasingly active topic in the last two decades. In this review, we will summarize the main methods for the synthesis of thiocarboxylates, which might provide general ideas to access more effective thioester-based drugs.

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Methods for the direct synthesis of thioesters from aldehydes: a focus review

Cited by 34 publications

References 67 publications

Palladium-Catalyzed Thiocarbonylation of Alkenes toward Linear Thioesters

Palladium-Catalyzed Thiocarbonylation of Alkenes toward Linear Thioesters

Cause Clarification of Cysteine Oxidation by Active Species Generated during the Oxidation Process of Cinnamaldehyde and Impact on an In Chemico Alternative Method for Skin Sensitization Using a Nucleophilic Reagent Containing Cysteine

A Recent Progress for the Synthesis of Thiocarboxylates

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