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Abstract
Sulfur-containing heterocycles are currently attracting a
great deal of interest in several diverse fields. For instance, substituted tetrahydrothiophenes[1] have received considerable attention due to their extremely wide-ranging chemical and biological applications.[2] These include their use as potent a-glucosidase inhibitors,[3] as an inhibitor of copper amine oxidases[4] and as selective A3 agonists and antagonists.[5] In addition, they have been utilised in chemical transformations, such as catalytic asymmetric epoxidation, catalytic intramolecular cyclopropanation, and asymmetric metal catalysis hydrogenation.[6] From a nanochemical perspective,
the adsorption chemistries and physical properties
of 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 aromatic
and heterocyclic compounds. It is usually achieved by
the utilisation of commercially accessible organolithiums (or lithium amides); however, these reactions do have their
drawbacks, including the intolerance of certain functional
groups, the need for cryoscopic temperatures and the inadvertent reactivity with polar reaction solvents.
Original language | English |
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Pages (from-to) | 8600-8604 |
Number of pages | 4 |
Journal | Chemistry - A European Journal |
Volume | 16 |
Issue number | 29 |
DOIs | |
Publication status | Published - 2010 |
Keywords
- magnesiation
- thiophene
- tetrahydrothiophene
- furan
- tetrahydrofuran
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Projects
- 3 Finished