Abstract
| Language | English |
|---|---|
| Pages | 8600-8604 |
| Number of pages | 4 |
| Journal | Chemistry - A European Journal |
| Volume | 16 |
| Issue number | 29 |
| DOIs | |
| Publication status | Published - 2010 |
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Keywords
- magnesiation
- thiophene
- tetrahydrothiophene
- furan
- tetrahydrofuran
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Sodium-mediated magnesiation of thiophene and tetrahydrothiophene: structural contrasts with furan and tetrahydrofuran. / Blair, V.L.; Kennedy, A.R.; Mulvey, R.E.; O'Hara, C.T.; EPSRC (Funder).
In: Chemistry - A European Journal, Vol. 16, No. 29, 2010, p. 8600-8604.Research output: Contribution to journal › Article
TY - JOUR
T1 - Sodium-mediated magnesiation of thiophene and tetrahydrothiophene: structural contrasts with furan and tetrahydrofuran
AU - Blair, V.L.
AU - Kennedy, A.R.
AU - Mulvey, R.E.
AU - O'Hara, C.T.
AU - EPSRC (Funder)
PY - 2010
Y1 - 2010
N2 - 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.
AB - 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.
KW - magnesiation
KW - thiophene
KW - tetrahydrothiophene
KW - furan
KW - tetrahydrofuran
UR - http://www.scopus.com/inward/record.url?scp=77955196595&partnerID=8YFLogxK
UR - http://dx.doi.org/10.1002/chem.201001139
U2 - 10.1002/chem.201001139
DO - 10.1002/chem.201001139
M3 - Article
VL - 16
SP - 8600
EP - 8604
JO - Chemistry - A European Journal
T2 - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 29
ER -