Synthesis and spectral properties of 1-aryl-2-formylpyrroles

del, María Milagros; Pina, K.; Budylin, V. A.; Rodriges, M.; Терентьев, П. Б.; Bundel, Yu. G.

doi:10.1007/bf00479906

Cited by 3 publications

(4 citation statements)

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“…Following these encouraging results, we decided to extend our study to pyrrole- and thiophene-based 2-imino heterocyclopentadienes (Scheme , bottom). First, pyrrole 2-carboxaldehyde was considered as a suitable starting substrate, given its direct availability from furfural via the Paal–Knorr synthesis or via a three-step sequence (carbonyl reduction/Achmatowicz rearrangement/Maillard condensation) . Indole and thiophene 2-carboxaldehydes were also included, to assess the scope of the coupling within the heterocyclopentadiene family.…”

Section: Resultsmentioning

confidence: 99%

Redox-Neutral Ru(0)-Catalyzed Alkenylation of 2-Carboxaldimine-heterocyclopentadienes

et al. 2022

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A new Ru 3 (CO) 12 -catalyzed directed alkenylation of 2-carboxaldimine-heterocyclopentadienes has been accomplished. This process allows to couple furan, pyrrole, indole and thiophene 2-carboxaldimines with electron-poor alkenes such as acrylates, vinylsulfones, and styrenes. This regio-and chemoselective oxidative C-H coupling does not require the presence of an additional sacrificial oxidant. Density functional theory (DFT) calculations allowed to propose a mechanism and unveiled the nature of the H 2 acceptor.

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Section: Resultsmentioning

confidence: 99%

Redox-Neutral Ru(0)-Catalyzed Alkenylation of 2-Carboxaldimine-heterocyclopentadienes

et al. 2022

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“…Pyrrole 2‐carboxaldehyde was another substrate considered for our carbonylative study (Figure d). Given its accessibility from furfural in one step, through a Paal‐Knorr synthesis, or in three steps through a carbonyl reduction/Achmatowicz rearrangement/Maillard condensation sequence, this substrate can be regarded as a biomass‐derived building block, too. Extension to thiophene 2‐carboxaldehyde was also envisaged, to verify the generality of the heterocyclopentadiene family (Figure e).…”

Section: Introductionmentioning

confidence: 99%

Ru‐Catalyzed Carbonylative Murai Reaction: Directed C3‐Acylation of Biomass‐Derived 2‐Formyl Heteroaromatics

et al. 2020

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The Murai reaction is a ruthenium‐catalyzed transformation leading to alkylated arenes through the C−C bond formation between an alkene and an arene bearing a directing group. Discovered in the nineties, this useful C−H activation based coupling has been the object of intense study since its discovery. After having studied the Murai reaction on 2‐formylfurans of biomass derivation, we describe here the carbonylative version applied to 2‐formylfurans, 2‐formylpyrrols and 2‐formylthiophenes. This acylation reaction takes place regioselectively at C3 position of the heterocyclopentadienes thanks to the installation of removable imine directing groups. The transformation can be achieved by treating the two reaction partners with a catalytic amount of Ru3(CO)12, in toluene at 120–150 °C, after CO bubbling, at atmospheric pressure. DFT computations of the full catalytic cycle help in deciphering the mechanism of this transformation, and to rationalize the different behaviors depending on the nature of imine directing groups.

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“…Given its accessibility from furfural in one step, through a Paal-Knorr synthesis, 36 or in three steps through a reduction/Achmatowicz rearrangement/Maillard condensation sequence, 37 this substrate can be regarded as a biomass-derived building block, too. Extension to thiophene 2-carboxaldehyde was also envisaged, to verify the generality of the heterocyclopentadiene family.…”

mentioning

confidence: 99%

“…Although some TMcatalyzed direct functionalizations of pyrrole or thiophene 2-carboxaldehydes have been reported, these studies have mainly addressed C5-arylation [38][39][40][41] and C5-alkylation, 23 while the C3-functionalization has been only very marginally explored. [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] Herein, we disclose the first C3-carbonylative versions of the Murai reaction on furfural derivatives, pyrrole 2-carboxaldehydes and their benzo-fused analogs -indoles -as well as on thiophene 2carboxaldehydes, through their corresponding aldimines, which act as removable directing groups.…”

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confidence: 99%

Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics

Sala¹,

Roudesly²,

Veiros³

et al. 2019

Preprint

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We describe here the carbonylative Murai reaction applied to 2-formylfurans, 2-formylpyrrols and 2-formylthiophenes. Thanks to the installation of removable imine directing groups, this acylation reaction takes place regioselectively at C3 position of the heterocyclopentadienes. It can be achieved by treating the two reaction partners with a catalytic amount of Ru3(CO)12, in toluene at 120-150 °C, after CO bubbling, at atmospheric pressure. DFT computations of the full catalytic cycle help in deciphering the mechanism of this transformation, and to rationalize the different behaviors depending on the nature of imine directing groups.

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Synthesis and spectral properties of 1-aryl-2-formylpyrroles

Cited by 3 publications

References 9 publications

Redox-Neutral Ru(0)-Catalyzed Alkenylation of 2-Carboxaldimine-heterocyclopentadienes

Redox-Neutral Ru(0)-Catalyzed Alkenylation of 2-Carboxaldimine-heterocyclopentadienes

Ru‐Catalyzed Carbonylative Murai Reaction: Directed C3‐Acylation of Biomass‐Derived 2‐Formyl Heteroaromatics

Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics

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