One-Pot Reaction of Carboxylic Acids and Ynol Ethers for The Synthesis of β-Keto Esters

Zeng, Lieguang; Lai, Zhencheng; Cui, Sunliang

doi:10.1021/acs.joc.8b02715

Cited by 22 publications

(14 citation statements)

References 43 publications

(33 reference statements)

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“…16 Subsequently, cyclization and methylation smoothly gave isoxazolone 47 in two steps. 17 To obtain more insight into the transformation mechanism, the kinetic isotope effect was determined by two parallel experiments with 1a and 1a-d 15 with 2a under the standard conditions. The resulting value of k H /k D = 6.0 indicates that cleavage of the C−H bond is probably involved in the turnover-limiting step (Scheme 5a).…”

Section: Cluster Synlettmentioning

confidence: 99%

“…Recently, transition metal-catalyzed ortho C−H activation strategy has been rapidly developed and achieved enormous successes by employing different kinds of directing groups with coordinating properties towards metal species. 5 Among diazocarbonyl compounds participanted in ortho C-H bond activation/carbene insertion have also been successfully explored and made significant progress. 6 In our research group, we are interested in the phosphorous oxide directed C-H functionzlizations in the past several years.…”

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confidence: 99%

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Iridium(III)-Catalyzed C−H Functionalization of Triarylphosphine Oxides with Diazo Dicarbonyl Compounds: Synthesis of α-Aryl 1,3-Dicarbonyl Derivatives

Lou¹,

Li²,

Yang³

2021

Synlett

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Section: Cluster Synlettmentioning

confidence: 99%

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confidence: 99%

Iridium(III)-Catalyzed C−H Functionalization of Triarylphosphine Oxides with Diazo Dicarbonyl Compounds: Synthesis of α-Aryl 1,3-Dicarbonyl Derivatives

Lou¹,

Li²,

Yang³

2021

Synlett

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“…In 2018, the Cui group devised a one‐pot synthesis of β ‐keto esters 31.1 from addition 31.2 /rearrangement 31.3 between ynol ethers and arylacetic acids (Eq. 31‐1).…”

Section: Nucleophilic Acidsmentioning

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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“…For many years silver(I) oxide has been widely used as a catalyst in different organic transformations, leading to the synthesis of a variety of organic molecules such as pyrroles, imidazolines, β-keto esthers, or benzothiophenes [1][2][3][4][5], as well as in many stoichiometric reactions, such as the synthesis of N-heterocyclic carbenes (NHC) based on Ag 2 O [6][7][8]. In spite of that, mechanistic studies of reactions involving Ag 2 O are really scarce, with some notable exceptions being those related to the ethylene epoxidation reaction [9][10][11] and the generation of NHC-Ag(I) complexes used in further transmetalation processes [12].…”

Section: Introductionmentioning

confidence: 99%

Ag2O versus Cu2O in the Catalytic Isomerization of Coordinated Diaminocarbenes to Formamidines: A Theoretical Study

Maelen

Ruiz

2022

Materials

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DFT theoretical calculations for the Ag2O-induced isomerization process of diaminocarbenes to formamidines, coordinated to Mn(I), have been carried out. The reaction mechanism found involves metalation of an N-H residue of the carbene ligand by the catalyst Ag2O and the formation of a key transition state showing a μ-η2:η2 coordination of the formamidinyl ligand between manganese and silver, which allows a translocation process of Mn(I) and silver(I) ions between the carbene carbon atom and the nitrogen atom, before the formation of the formamidine ligand is completed. Calculations carried out using Cu2O as a catalyst instead of Ag2O show a similar reaction mechanism that is thermodynamically possible, but highly unfavorable kinetically and very unlikely to be observed, which fully agrees with experimental results.

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One-Pot Reaction of Carboxylic Acids and Ynol Ethers for The Synthesis of β-Keto Esters

Cited by 22 publications

References 43 publications

Iridium(III)-Catalyzed C−H Functionalization of Triarylphosphine Oxides with Diazo Dicarbonyl Compounds: Synthesis of α-Aryl 1,3-Dicarbonyl Derivatives

Iridium(III)-Catalyzed C−H Functionalization of Triarylphosphine Oxides with Diazo Dicarbonyl Compounds: Synthesis of α-Aryl 1,3-Dicarbonyl Derivatives

Arylacetic Acids in Organic Synthesis

Ag2O versus Cu2O in the Catalytic Isomerization of Coordinated Diaminocarbenes to Formamidines: A Theoretical Study

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