MnO<sub>2</sub>-promoted carboesterification of alkenes with anhydrides: a facile approach to γ-lactones

Wu, Lihuan; Zhang, Zhenming; Liao, Jianhua; Li, Jianxiao; Wu, Wanqing; Jiang, Huanfeng

doi:10.1039/c5cc08867d

Cited by 19 publications

(11 citation statements)

References 63 publications

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“…Furthermore, various intermolecular [2 + 2] type reactions such as the C–C/C–O bond formation of an alkene with an acetyl unit have also been investigated. Among them is a common and powerful method based on the generation of carbon radicals in a one-electron oxidation process using heavy metals (Scheme , bottom). , Recently, a methodology using photo-redox catalysts has also been developed . However, in intermolecular reactions, it is difficult to control the diastereoselectivity by changing only the reaction conditions, and only a few examples of this have been reported in the literature …”

Section: Introductionmentioning

confidence: 99%

trans-Diastereoselective Syntheses of γ-Lactones by Visible Light-Iodine-Mediated Carboesterification of Alkenes

2019

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This study aims to develop an intermolecular lactonization reaction of alkenes with carbonyls mediated by visible light and molecular iodine. The one-step reaction involved the carboesterification of alkenes to produce the corresponding lactones in moderate to good yield. It was also revealed that it is possible to control the diastereoselectivity of the reaction by altering the base used and the reaction conditions. When water was added as a solvent, the reaction resulted in the formation of lactones with trans-selectivity. A mechanistic investigation was undertaken and it was found that the reaction requires the generation of an iodine radical from molecular iodine, driven by visible light irradiation, and proceeds via the formation of an iodine radical alkene adduct. The proposed reaction is an example of a rare-metal free intermolecular addition cyclization reaction, which is an environment-friendly chemical process that only uses molecular iodine. In addition, since diastereoselectivity was observed without the use of any specific reagents, the developed methodology is an example of a novel stereoselective transformation using only cost-effective reagents.

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Section: Introductionmentioning

confidence: 99%

trans-Diastereoselective Syntheses of γ-Lactones by Visible Light-Iodine-Mediated Carboesterification of Alkenes

2019

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“…Especially, Pd-catalyzed oxidative cyclizations of alkenes to construct functionalized molecules have been well explored . In this regard, as commercial materials, carboxylic acids/anhydrides have been extensively explored in alkenyl C–H bond functionalization for the synthesis of heterocycles, in which they are generally used as synthons by offering one or two bonding sites . For instance, Ackermann reported the Ru-catalyzed C–H bond alkenylation between benzoic acids and active alkenes with the formation of C–O bond (Scheme , I) .…”

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confidence: 99%

Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones

Huang

Zheng

et al. 2017

J. Org. Chem.

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The first example of Pd-catalyzed oxidative cyclization of allyltosylamides with acetic acid is reported. This transformation involved C-N/C-C bond formation and provided 3-pyrrolin-2-ones in a one-pot manner with easy-operation, excellent atom economy and good yields. Mechanistic studies indicate that the reaction proceeds through intermolecular aminopalladation, migratory insertion, reinsertion and β-hydride elimination processes.

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“…synthesis of lactones, aldehydes, etc.) [47][48][49][50][51][52][53][54] and (ii) sustainable chemistry and environmental remediation, involving highly interesting reactions such as oxygen-evolution reaction (OER), VOC degradation, syngas reactions, biofuel production, etc. [26,[55][56][57][58][59].…”

Section: Formmentioning

confidence: 99%

Recent Manganese Oxide Octahedral Molecular Sieves (OMS–2) with Isomorphically Substituted Cationic Dopants and Their Catalytic Applications

Sabaté

Sabater

2021

Catalysts

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The present report describes the structural and physical–chemical variations of the potassium manganese oxide mineral, α–MnO2, which is a specific manganese octahedral molecular sieve (OMS) named cryptomelane (K–OMS–2), with different transition metal cations. We will describe some frequently used synthesis methods to obtain isomorphic substituted materials [M]–K–OMS–2 by replacing the original manganese cationic species in a controlled way. It is important to note that one of the main effects of doping is related to electronic environmental changes, as well as to an increase of oxygen species mobility, which is ultimately related to the creation of new vacancies. Given the interest and the importance of these materials, here, we collect the most recent advances in [M]–K–OMS–2 oxides (M = Ag, Ce, Mo, V, Nb, W, In, Zr and Ru) that have appeared in the literature during the last ten years, leaving aside other metal–doped [M]–K–OMS–2 oxides that have already been treated in previous reviews. Besides showing the most important structural and physic-chemical features of these oxides, we will highlight their applications in the field of degradation of pollutants, fine chemistry and electrocatalysis, and will suggest potential alternative applications.

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MnO₂-promoted carboesterification of alkenes with anhydrides: a facile approach to γ-lactones

Abstract: An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.

Cited by 19 publications

References 63 publications

trans-Diastereoselective Syntheses of γ-Lactones by Visible Light-Iodine-Mediated Carboesterification of Alkenes

trans-Diastereoselective Syntheses of γ-Lactones by Visible Light-Iodine-Mediated Carboesterification of Alkenes

Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones

Recent Manganese Oxide Octahedral Molecular Sieves (OMS–2) with Isomorphically Substituted Cationic Dopants and Their Catalytic Applications

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MnO2-promoted carboesterification of alkenes with anhydrides: a facile approach to γ-lactones

Abstract: An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.

Cited by 19 publications

References 63 publications

trans-Diastereoselective Syntheses of γ-Lactones by Visible Light-Iodine-Mediated Carboesterification of Alkenes

trans-Diastereoselective Syntheses of γ-Lactones by Visible Light-Iodine-Mediated Carboesterification of Alkenes

Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones

Recent Manganese Oxide Octahedral Molecular Sieves (OMS–2) with Isomorphically Substituted Cationic Dopants and Their Catalytic Applications

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MnO₂-promoted carboesterification of alkenes with anhydrides: a facile approach to γ-lactones