Update 1 of: Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis

Sartori, Giovanni; Maggi, Raimondo

doi:10.1021/cr900316t

Cited by 21 publications

(28 citation statements)

References 359 publications

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“…The same authors also provided an exhaustive overview about the heterogeneous catalysis applied in the field of the protection and deprotection reactions of functional groups during the organic synthesis. Zeolites are also extensively employed in this field, and have the advantage of providing an easier reaction handling and final purification step, together with an improved selectivity obtained for the protective chemistry [11].…”

Section: Introductionmentioning

confidence: 99%

Zeolites as Acid/Basic Solid Catalysts: Recent Synthetic Developments

2019

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The zeolites are porous solid structures characterized by a particular framework of aluminosilicates, in which the incorporation of the Al+3 ions generates an excess of negative charge compensated by cations (usually alkali or alkali earth) or protons. In the latter case, they are employed as catalysts for a wide variety of reactions, such as dehydration, skeletal isomerization and cracking, while the catalytic activity of basic zeolites has not found, up to now, any industrial or whatever relevant application in chemical processes. In the present review, we firstly intend to give an overview of the fundamental chemical composition, as well as the structural features of the zeolite framework. The purpose of this paper is to analyze their key properties as acid, both Lewis and Brønsted, and basic solid support. Their application as catalysts is discussed by reviewing the already published works in that field, and a final remark of their still unexplored potential as green, mild, and selective catalyst is also reported.

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Section: Introductionmentioning

confidence: 99%

Zeolites as Acid/Basic Solid Catalysts: Recent Synthetic Developments

2019

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“…Various protecting groups like esters, silyl ethers, alkoxy alkyl ethers, and so forth have been reported for the protection of alcohols ( Figure 1 ). 1 However, tert -butyl ether is one of the most versatile protecting group because of its extreme stability in basic conditions. 2 It can be successfully employed to aliphatic alcohols as well as phenols and is compatible with other protecting groups and functionalities such as carbonyls, nitriles, hydroxyl moieties, and esters.…”

Section: Introductionmentioning

confidence: 99%

Yb(OTf)₃-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions

et al. 2020

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Protecting group chemistry has invariably captured the fascination of chemists because of its extensive viability in chemical synthesis. The present report describes our pioneer work of applying ytterbium triflate as a catalyst, for the reaction of alcohols with di- tert -butyl dicarbonate (Boc 2 O) leading to the formation of tert -butyl ethers. There exists no recorded evidence for the use of Yb(OTf) 3 as a catalyst for the protection of alcohols to tert -butyl ethers, despite its excellent utility in various reactions. Yb(OTf) 3 has been used predominantly in the catalytic deprotection studies such as selective deprotection of tert -butyl esters to carboxylic acids as well as prenyl ethers to alcohols. This study involved the critical evaluation of solvent, time, and temperature that finally led to an efficient protocol for the formation of tert -butyl ethers. Yb(OTf) 3 catalyzed the formation of tert -butyl ethers, notably reducing the reaction time, which is exemplified by the achievement of up to 92% conversion of alcohols to tert -butyl ethers within an hour. Additionally, the report demonstrates the utility of this synthetic protocol for the protection of carboxylic acids.

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“…Heterogeneous catalysts have some advantages such as easy separation from the reaction mixture, recyclability, non-toxicity, ease of use, storage safety, long shelf-life, and tolerance of a wide range of temperatures and pressures [1][2][3]. Heterogeneous organic transformations have been recently performed with immobilized reagents on solid supports such as charcoal, alumina, silica, and polymers.…”

Section: Introductionmentioning

confidence: 99%

“…Nowadays, because of an increase in environmental awareness in chemical research and industry, attention has been focused on the replacement of conventional Brønsted and Lewis acid catalysts with reusable heterogeneous catalysts. Heterogeneous catalysts have some advantages such as easy separation from the reaction mixture, recyclability, non‐toxicity, ease of use, storage safety, long shelf‐life, and tolerance of a wide range of temperatures and pressures . Heterogeneous organic transformations have been recently performed with immobilized reagents on solid supports such as charcoal, alumina, silica, and polymers.…”

Section: Introductionmentioning

confidence: 99%

A Novel One‐pot Protocol for Silica Sodium Carbonate‐Catalyzed Synthesis of Pyrano[2,3‐h]coumarins

Farahi

Karami

Tanuraghaj

et al. 2017

Journal of Heterocyclic Chem

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Update 1 of: Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis

Cited by 21 publications

References 359 publications

Zeolites as Acid/Basic Solid Catalysts: Recent Synthetic Developments

Zeolites as Acid/Basic Solid Catalysts: Recent Synthetic Developments

Yb(OTf)₃-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions

A Novel One‐pot Protocol for Silica Sodium Carbonate‐Catalyzed Synthesis of Pyrano[2,3‐h]coumarins

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Update 1 of: Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis

Cited by 21 publications

References 359 publications

Zeolites as Acid/Basic Solid Catalysts: Recent Synthetic Developments

Zeolites as Acid/Basic Solid Catalysts: Recent Synthetic Developments

Yb(OTf)3-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions

A Novel One‐pot Protocol for Silica Sodium Carbonate‐Catalyzed Synthesis of Pyrano[2,3‐h]coumarins

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Yb(OTf)₃-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions