On-surface multicomponent Povarov reaction examined by paper spray mass spectrometry

Pimenta, João Victor Coelho; Sabino, Adão A.; Augusti, Rodinei

doi:10.1016/j.ijms.2021.116775

Cited by 4 publications

(4 citation statements)

References 16 publications

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“…They discovered the role of hydrogen bonding in significantly flattening the energy barrier at the air‐liquid interface. Recently, Pimenta et al [33] . employed paper spray ionization mass spectrometry (PSI‐MS) to investigate the on‐surface Povarov reaction, and they believed that PSI‐MS can be widely used to investigate similar on‐surface organic reactions.…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐Free Three‐Component Petasis Reactions Accelerated in Microdroplets: Reaction Optimization and Senstive Detection by Mass Spectrometry

Jin

Sun

et al. 2023

Analysis & Sensing

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Due to their important roles in medicine, the product of the Petasis reaction has attracted extensive interest in pharmaceutical, medical and chemical communities. Traditional three‐component Petasis methods normally use various catalysts under harsh conditions (high temperature, microwave, etc.) for long reaction times. In this study, we developed a green and highly efficient microdroplet method for accelerating the Petasis reaction, which obtain good yields without the need of any catalysts under mild reaction conditions. The Petasis reaction in microdroplets was suitable for a variety of salicylaldehydes, arylboronic acids and amines. The Petasis reaction in microdroplets was accelerated by approximately 4 orders of magnitude by comparing the measured rate constants in bulk. Further, a scaled‐up amount of 0.8 g h−1 was achieved for the Petasis reaction in microdroplets. This study supplies not only a high‐efficiency and environment‐friendly methodology to constructing aryl amines in organic community but also a useful derivatization strategy for highly sensitive mass spectrometric detection of arylboronic acids and aryl aldehydes.

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Section: Introductionmentioning

confidence: 99%

Catalyst‐Free Three‐Component Petasis Reactions Accelerated in Microdroplets: Reaction Optimization and Senstive Detection by Mass Spectrometry

Jin

Sun

et al. 2023

Analysis & Sensing

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“…63 The above-mentioned features of microdroplet chemistry have encouraged preliminary explorations of multicomponent reactions in microdroplets. Until now, threecomponent Biginelli, 64 Hantzsch, 65 Mannich, 41,66 Betti, 67 Povarov, 68 and Petasis reactions 69 and a five-component spiro-pyrrolidine construction 38 have been unlocked by microdroplet chemistry, where the three-component Passerini reaction has not yet been uncovered. Additionally, the above MCR examples were limited to milligram-scale synthesis except the Betti reaction 67 and Petasis reaction, 69 restricting the applicability of microdroplet chemistry in MCRs.…”

Section: ■ Introductionmentioning

confidence: 99%

Microdroplet Chemistry Accelerating a Three-Component Passerini Reaction for α-Acyloxy Carboxamide Synthesis

Cheng

et al. 2023

J. Org. Chem.

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α-Acyloxy carboxamides are important multifunctional natural products that show bioactive and pharmacological activities. Traditional three-component Passerini reactions among isocyanates, aldehydes/ketones, and carboxylic acids for affording α-acyloxy carboxamides suffer from several drawbacks such as long reaction time, high reaction temperature, special reaction devices, etc. Herein, we developed a high-efficiency microdroplet method for accelerating the Passerini reactions by 3 orders of magnitude by comparing with the rate constants in bulk, achieving high-yield and gram-scale (scaling up to 1.91 g for 1 h collection) synthesis of αacyloxy carboxamides at near room temperature. The Passerini microdroplet method shows a wide scope for a variety of benzoic acids, aryl aldehydes, and isocyanates. Moreover, the Passerini reaction was poorly conducted in aqueous microdroplets but well accelerated in acetonitrile microdroplets with at least 230 times efficiency than on-water Passerini reactions. All results proved it an attractive alternative to classic organic synthesis for the construction of α-acyloxy carboxamides and derivatives.

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“…Owing to the lack of easily ionized chemical groups, general brominated organic compounds are difficult to ionize by matrix-assisted laser desorption ionization (MALDI), electrospray ionization (ESI), paper spray ionization, and other ambient ionization sources, leading to low-sensitivity in MS analysis. With the benefits of low cost, no sample pretreatment, minimal matrix effect, and high analytical efficiency, PSI-MS has been commonly used in clinical diagnosis, − environmental analysis, and reaction monitoring. ,,− To improve the sensitivity of weakly polar and nonpolar substances by MS detection, online derivatization of the target analytes has been integrated into PSI (termed as reactive PSI). Huang’s group quantitatively determined quinones in complex samples by reactive PSI-MS, where quinones were in situ derivatized with cysteamine to significantly improve the ionization efficiency of quinones.…”

Section: Introductionmentioning

confidence: 99%

Suzuki C–C Coupling in Paper Spray Ionization: Microsynthesis of Biaryls and High-Sensitivity MS Detection of Aryl Bromides

Lin

Xue

Sun

et al. 2022

J. Am. Soc. Mass Spectrom.

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Suzuki–Miyaura cross-coupling is one of the most powerful strategies for constructing biaryl compounds. However, classic Suzuki–Miyaura coupling suffers from hour-scale reaction time and competitive protodeboronation. To address these problems, a mild nonaqueous potassium trimethylsilanolate (TMSOK)-assisted Suzuki–Miyaura coupling strategy was designed for the microsynthesis of biaryls in paper spray ionization (PSI). Due to the acceleration power facilitated by microdroplet chemistry in reactive PSI, the microsynthesis of biaryls by reactive PSI was accomplished within minutes with comparable yields to the bulk, showing good substrate applicability from 32 Suzuki–Miyaura reactions of aryl bromides and aryl boronic acid/borates bearing different substituents. Based on the above TMSOK-assisted Suzuki–Miyaura coupling strategy, we further developed a high-sensitivity and selective PSI mass spectrometry (MS) method for quantitative analysis of aryl bromides, a class of environmentally persistent organic pollutants that cannot be directly detected by ambient mass spectrometry due to their low ionization efficiency. In situ derivatization of aryl bromides was achieved with aryl borates bearing quaternary ammonium groups in PSI. The proposed PSI-MS method shows good linearity over the 0.01–10 μmol L–1 range with low detection limits of 1.8–4.8 nmol L–1 as well as good applicability to the rapid determination of six aryl bromides in three environmental water samples. The proposed PSI-MS method also shows good applicability to brominated flame retardants (polybrominated diphenyls/diphenyl esters). Overall, this study provides a simple, rapid, low-cost, high-sensitivity, and high-selectivity strategy for trace aryl bromides and other brominated pollutants in real samples with minimal/no sample pretreatment.

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On-surface multicomponent Povarov reaction examined by paper spray mass spectrometry

Cited by 4 publications

References 16 publications

Catalyst‐Free Three‐Component Petasis Reactions Accelerated in Microdroplets: Reaction Optimization and Senstive Detection by Mass Spectrometry

Catalyst‐Free Three‐Component Petasis Reactions Accelerated in Microdroplets: Reaction Optimization and Senstive Detection by Mass Spectrometry

Microdroplet Chemistry Accelerating a Three-Component Passerini Reaction for α-Acyloxy Carboxamide Synthesis

Suzuki C–C Coupling in Paper Spray Ionization: Microsynthesis of Biaryls and High-Sensitivity MS Detection of Aryl Bromides

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