Pot‐Economical Synthesis of Hydroxylated Arylethenyl‐arylethynyl‐arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions

Shard, Amit; Kumar, Rajesh; Equbal, Danish; Sinha, Arun K.

doi:10.1002/ajoc.201700504

Cited by 3 publications

(3 citation statements)

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“…As one of the important organic reactions, − decarboxylation helps to synthesize new compounds containing C–C or C–X (X = N, P, O) bonds via heterocyclic synthesis. − Moreover, the decarboxylation reaction also provides cost-effective raw materials for the synthesis of new carbon skeletons due to the low price, low toxicity, and high stability of the carboxylic acid compounds . As a result, the decarboxylation reaction has been widely used in the fields of drug synthesis, , chemical industry, , and biology. − At present, decarboxylation reactions are mainly catalyzed by toxic and/or expensive organometallic compounds, − and the reactions are usually carried out in an organic base , and at a high temperature. , …”

Section: Introductionmentioning

confidence: 99%

Molecular Coadsorption of p-Hydroxythiophenol on Silver Nanoparticles Boosts the Plasmon-Mediated Decarboxylation Reaction

et al. 2022

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Surface plasmons have received much attention in chemical reactions because of their high light-utilizing efficiency, high reaction rate, and mild reaction conditions. However, the potential of plasmonic photochemistry has not been fully exploited, mainly due to the limited lifetime of plasmongenerated hot carriers. Herein, using in situ Raman spectroscopy, we reveal that the coadsorption of p-hydroxythiophenol (PHTP) molecules significantly accelerates the plasmon-mediated decarboxylation reaction of p-mercaptobenzoic acid adsorbed on silver nanoparticles. The observed boosting of the decarboxylation reaction is attributed to the matched energy distribution of the plasmon-generated hot electrons to the lowest unoccupied molecular orbital (LUMO) level of the coadsorbed PHTP molecules. Our findings will help not only to deepen the understanding of the plasmon-mediated chemical reactions but also to fabricate highly efficient plasmonic catalysts conveniently and costeffectively.

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Section: Introductionmentioning

confidence: 99%

Molecular Coadsorption of p-Hydroxythiophenol on Silver Nanoparticles Boosts the Plasmon-Mediated Decarboxylation Reaction

et al. 2022

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“…Shortly thereafter, Sinha and co-workers 105 developed an economical sequential decarboxylative Perkin condensation/ Sonogashira coupling strategy using polyethylene glycol (PEG) as a solvent (Scheme 29). To form the desired alkene products 70, the precursor of the Sonogashira coupling, stilbene intermediate int-25, was obtained in situ by decarboxylation of a carboxylic acid (68) and an aldehyde (69) in the presence of MIM/piperidine under MW irradiation.…”

Section: Metal-free Decarboxylation Strategiesmentioning

confidence: 99%

Microwave-assisted decarboxylative reactions: advanced strategies for sustainable organic synthesis

et al. 2022

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“…Piperidine and Et 3 N were mostly used. Sinha and co‐workers presented a study on the sequential Perkin‐Sonogashira reactions in one pot towards the synthesis of highly π‐conjugated complex arylethenyl‐arylethynyl‐arenes. The process avoided protection‐deprotection manipulations.…”

Section: Nucleophilic Methylenesmentioning

confidence: 99%

Arylacetic Acids in Organic Synthesis

et al. 2019

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Arylacetic acids are widely used in organic reactions and their recent advances are summarized in six categories according to their triggered pathways: (1) the acid as directing group in ortho-or meta-CÀ H activation; (2) decarboxylation; (3) deprotonation; (4) nucleophilic methylenes; (5) nucleophilic acids; (6) electrophilic acids. Reactions with alkenes, alkynes, aldehydes, amines, water, Grignard reagents, silanes and so forth are discussed. We hope this Minireview will promote future research in this area. Recently, the Zeng group [3g] reported a weakly coordinationassisted alkynylation of arylacetic acids with iridium catalysis under air atmosphere (Eq. 2-2). It was supported the sixmembered ring cycloiridiated 2.5 acted as the key intermediate. The alkynylation of indole, thiophene, pyrrole, and benzo[b] thiophene afforded better yields than phenylacetic acids. The acid moiety could also participated in the intramolecular ortho-CÀ H activation, which was developed by the Shi group to obtain lactonization 2.6 (Eq. 2-3) (Scheme 2). Meta-CÀ H ArylationThe study of Yu group [3e] in 2017 revealed a successful control of meta selectivity 3.1 of arylation from aryl iodides (Eq. 3-1). The use of mono-protected 3-amino-2-hydroxypyridine (as ligand) and 2-carbomethoxynorbornene (NBE-CO 2 Me) were crucial. In the absence of NBE-CO 2 Me, only ortho-arylated product was obtained. This method was still efficient in a gramsale (Scheme 3). Decarboxylation Decarboxylative CouplingAs shown in Scheme 4, the decarboxylation could generate benzyl radicals 4.1. Then, direct couplings of 4.1 with diverse [ + ] These authors contributed equally. Scheme 1. Six categories based on triggered mechanism. 2 3 4 5 6 7 8 . Passerini Three-Component ReactionThe Passerini reaction was the oldest multicomponent reaction (MCR) [37d] in which isocyanides, carboxylic acids and aldehydes were used. It was powerful for the rapid construction of complex molecules. The tactic to expand the scope of Passerini reaction was to use surrogates of the carbonyl partners. As described in Scheme 51, syn-chlorooximes, [37b] diazoketones, [37c] alcohols, [37d,e] azirines [37f] and isatins [37g] could be employed instead of aryl or alkyl aldehydes [37a] (Scheme 51). Besides, in 2018, Zhang and co-workers [37] have firstly reported asymmetric phosphoric acid-catalyzed four-component Ugi reaction, which Scheme 45. BTM-catalyzed cycloaddition. Scheme 46. HBTM-catalyzed cycloaddition. Scheme 47. TFA-catalyzed reaction. Scheme 48. Friedel-Crafts triggered tandem reactions. Scheme 49. C-acylation of 1,3-diones. Scheme 50. C-acylation of 1,3-indandiones.

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Pot‐Economical Synthesis of Hydroxylated Arylethenyl‐arylethynyl‐arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions

Abstract: As imple, economical and one-pot protocol is developed for construction of multiple carbon-carbon bonds having C(sp 2

Cited by 3 publications

References 74 publications

Molecular Coadsorption of p-Hydroxythiophenol on Silver Nanoparticles Boosts the Plasmon-Mediated Decarboxylation Reaction

Molecular Coadsorption of p-Hydroxythiophenol on Silver Nanoparticles Boosts the Plasmon-Mediated Decarboxylation Reaction

Microwave-assisted decarboxylative reactions: advanced strategies for sustainable organic synthesis

Arylacetic Acids in Organic Synthesis

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