Oxidative Cyclorelease from Soluble Polymeric Supports

Liu, Hua; Wan, and Shuangyi; Floreancig, Paul E.

doi:10.1021/jo0480951

Cited by 17 publications

(7 citation statements)

References 40 publications

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“…In our first attempt, we treated 1-octanol with THF and Amberlyst-15 under the same reaction conditions. The corresponding THF ether 7,16,17 (Table 2, entry 1) was formed in low yield. Similarly, 1-pentanol, 7 cyclohexanol, 5,7,9,17 isobutanol, 9 and tert-butanol 14 also gave the corresponding THF ethers (Table 2).…”

Section: Scheme 1 Literature Synthesis Of 2-aryltetrahydrofuransmentioning

confidence: 99%

Amberlyst-15-Catalyzed One-Pot Synthesis of 2-Aryltetrahydrofurans from Tetrahydrofuran

Gündüz

Kumbaracı

Talınlı

2012

Synlett

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The conversion to tetrahydropyranyl (THP) or tetrahydrofuranyl (THF) ethers are a part of an important method for protecting alcohol functional groups. It is well known that, in comparison with THP ethers, THF ethers have the advantage that they can be hydrolyzed under even milder acidic conditions and also they can be selectively cleaved in the presence of THP 1 ethers. In present study, a simple and one step route for the conversion of naphthols and phenols with tetrahydrofuran into corresponding 2-aryltetrahydrofurans using Amberlyst-15 as a catalyst is reported. This is the first example of the acid mediated formation and rearrangement reactions of tetrahydrofuranyl ether prepared from the tetrahydrofuran and aromatic/aliphatic hydroxy compounds. Scheme 1. A plausible reaction mechanism

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Section: Scheme 1 Literature Synthesis Of 2-aryltetrahydrofuransmentioning

confidence: 99%

Amberlyst-15-Catalyzed One-Pot Synthesis of 2-Aryltetrahydrofurans from Tetrahydrofuran

Gündüz

Kumbaracı

Talınlı

2012

Synlett

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“…Floreancig’s group [ 48 , 49 ] used an oxidative release (often cyclorelease) on the appropriate polymer-supported precursors. The mechanism involved in the oxidative cleavage is presented in Scheme 43 .…”

Section: Solid-supported Reagents Resins and Linkersmentioning

confidence: 99%

From Polymer to Small Organic Molecules: A Tight Relationship between Radical Chemistry and Solid-Phase Organic Synthesis

Mirizzi

Pulici

2011

Molecules

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Since Gomberg’s discovery of radicals as chemical entities, the interest around them has increased through the years. Nowadays, radical chemistry is used in the synthesis of 75% of all polymers, inevitably establishing a close relationship with Solid-Phase Organic Synthesis. More recently, the interest of organic chemists has shifted towards the application of usual “in-solution” radical chemistry to the solid-phase, ranging from the use of supported reagents for radical reactions, to the development of methodologies for the synthesis of small molecules or potential libraries. The aim of this review is to put in perspective radical chemistry, moving it away from its origin as a synthetic means for solid supports, to becoming a useful tool for the synthesis of small molecules.

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“…This process is driven by electrophile quenching through a facile proton or 2-tetrahydropyranyl cation loss rather than through nucleophilic addition. 35 Wangyang Tu, a current graduate student, is further expanding upon the observation that arenes can tolerate a wide range of substituents to develop an oxidative fragmentation that is initiated by intramolecular transfer.…”

Section: Development Of Carbon-carbon Bond Forming Processesmentioning

confidence: 99%

Development and Applications of Electron-Transfer-Initiated Cyclization Reactions

Floreancig¹

2007

Synlett

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This account describes the work done by my group on electron-transfer-initiated cyclization reactions. In this work radical-cation formation initiates bond cleavage processes that form electrophilic groups leading to reactions with pendent nucleophiles to form cyclic structures. The discussion begins with an overview of the relevant concepts that inspired the work and opportunities that single-electron oxidation provides. Our early work in which we optimized the procedure, elucidated the mechanism, and determined the scope of the process will be discussed in detail, followed by applications that were devised based on these studies. 1 Introduction 2 Reaction Optimization and Mechanistic Studies 3 Applications to Heterocycle Synthesis through Carbon-Heteroatom Bond Formation 4 Development of Carbon-Carbon Bond-Forming Processes 5 Summary and Future Prospects

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Oxidative Cyclorelease from Soluble Polymeric Supports

Cited by 17 publications

References 40 publications

Amberlyst-15-Catalyzed One-Pot Synthesis of 2-Aryltetrahydrofurans from Tetrahydrofuran

Amberlyst-15-Catalyzed One-Pot Synthesis of 2-Aryltetrahydrofurans from Tetrahydrofuran

From Polymer to Small Organic Molecules: A Tight Relationship between Radical Chemistry and Solid-Phase Organic Synthesis

Development and Applications of Electron-Transfer-Initiated Cyclization Reactions

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