Sodium-mediated magnesiation of thiophene and tetrahydrothiophene : structural contrasts with furan and tetrahydrofuran
Blair, Victoria L. and Kennedy, Alan R. and Mulvey, Robert E. and O'Hara, Charles T. (2010) Sodium-mediated magnesiation of thiophene and tetrahydrothiophene : structural contrasts with furan and tetrahydrofuran. Chemistry - A European Journal, 16 (29). pp. 8600-8604. ISSN 1521-3765 (https://doi.org/10.1002/chem.201001139)
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Abstract
Sulfur-containing heterocycles are currently attracting agreat deal of interest in several diverse fields. For instance, substituted tetrahydrothiophenes have received considerable attention due to their extremely wide-ranging chemical and biological applications.These include their use as potent a-glucosidase inhibitors, as an inhibitor of copper amine oxidases and as selective A3 agonists and antagonists. In addition, they have been utilised in chemical transformations, such as catalytic asymmetric epoxidation, catalytic intramolecular cyclopropanation, and asymmetric metal catalysis hydrogenation. From a nanochemical perspective,the adsorption chemistries and physical propertiesof various thiophenes and tetrahydrothiophenes on gold surfaces have recently come to the fore.[7] Polythiophenes are also key compounds in modern materials research, currently utilised in, for example, the fabrication of semi-conducting, fluorescent, and electronic and optoelectronic materials.[8]In this work, metallation (exchange of a hydrogen atom with a metal atom) of the parent heterocycles, tetrahydrothiophene (THT) and thiophene is considered. Metallation is one of the most fundamental reactions in modern day synthesis and is a key tool in the preparation of functionalised aromaticand heterocyclic compounds. It is usually achieved bythe utilisation of commercially accessible organolithiums (or lithium amides); however, these reactions do have theirdrawbacks, including the intolerance of certain functionalgroups, the need for cryoscopic temperatures and the inadvertent reactivity with polar reaction solvents.
ORCID iDs
Blair, Victoria L., Kennedy, Alan R. ORCID: https://orcid.org/0000-0003-3652-6015, Mulvey, Robert E. ORCID: https://orcid.org/0000-0002-1015-2564 and O'Hara, Charles T.;-
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Item type: Article ID code: 28043 Dates: DateEvent2 August 2010Published29 July 2010Published Online29 April 2010AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Dr Charles Thomas O'Hara Date deposited: 03 Nov 2010 11:34 Last modified: 15 Sep 2024 00:41 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/28043