Recent Advances in the Chemistry of Thiophenes

Gronowitz, Salo

doi:10.1016/s0065-2725(08)60523-1

Cited by 99 publications

(15 citation statements)

References 441 publications

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“…A nickel phosphine catalyst was used to assist in the coupling. The 3-(10-undecenyl)thiophene was verified by 1 H and 13 C NMR, and the coupling constant data is consistent with literature results for 3-substituted thiophenes. All 1 H NMR and 13 C NMR spectra were recorded on a Bruker AC-300 at 300 and 75 MHz, respectively.…”

Section: Methodssupporting

confidence: 88%

Contact Angle and Electrochemical Characterization of Multicomponent Thiophene-Capped Monolayers

et al. 2000

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We have investigated the wetting behavior and electrochemical response of self-assembled monolayers made from ω-(3-thienyl)-alkyltrichlorosilanes and alkyltrichlorosilanes on indium-tin oxide coated glass slides. Contact angle measurements and cyclic voltammetry show that the properties of the monolayers change as the relative loading of the two components is changed by altering the concentration of the deposition solution. The water contact angles indicate that a fully loaded hydrophobic layer is formed, and both water and hexadecane contact angle measurements show that the tethered thiophenes are at the periphery of the monolayer. However, the hexadecane contact angles also imply that the surface roughness exposes the methylene groups of the monolayer chains. Cyclic voltammograms obtained from mixtures of 11-(3-thienyl)undecyltrichlorosilane and decyltrichlorosilane and mixtures of 16-(3-thienyl)hexadecyltrichlorosilane and hexadecyltrichlorosilane show that as the relative amount of thienyl-bearing chains in the monolayer decreases, the oxidation peak position shifts to higher potential and the peak area, which is related to the amount of charge transferred, decreases. Integration of the oxidation peak area from the cyclic voltammetry experiments yields a coverage that is consistent with a monolayer. Preliminary evidence for formation of a surface-tethered redox-active polymer is observed by cycling the self-assembled monolayers at low potentials.

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Section: Methodssupporting

confidence: 88%

Contact Angle and Electrochemical Characterization of Multicomponent Thiophene-Capped Monolayers

et al. 2000

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“…The “halogen dance” is a reaction in which halogen-substituted aromatics are isomerized [ 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 ]. Requiring a hindered lithium amide such as LiTMP, the reaction is driven by the stability of the arylmetal formed.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polysubstituted Ferrocenesulfoxides

et al. 2022

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The purpose of the study is to design synthetic methodologies, especially directed deprotometalation using polar organometallic reagents, to access polysubstituted ferrocenesulfoxides. From enantiopure 2-substituted (SiMe3, PPh2) S-tert-butylferrocenesulfoxides, a third substituent was first introduced at the 5 position (SiMe3, I, D, C(OH)Ph2, Me, PPh2, CH2NMe2, F) and removal of the trimethylsilyl group then afforded 2-substituted ferrocenesulfoxides unreachable otherwise. Attempts to apply the “halogen dance” reaction to the ferrocenesulfoxide series led to unexpected results although rationalized in light of calculated pKa values. Further functionalizations were also possible. Thus, new enantiopure, planar chiral di- and trisubstituted ferrocenes have been obtained, in addition to several original 2-substituted, 2,3- and 2,5-disubstituted, 2,3,5-trisubstituted and even 2,3,4,5-tetrasubstituted ferrocenesulfoxides, also enantiopure.

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“…From the perspective of operational safety, functional group compatibility, and further functionalization, we focused on the application of our recent work, which included a one-pot halogen dance/Negishi coupling, which allows regiocontrolled synthesis of multiple arylated thiophenes or furans. Compared with conventional stepwise transformations, the LDA (lithium diisopropylamide)-mediated halogen dance reaction leads to the formation of two chemical bonds in one pot, which reduces the number of reaction pots. Regardless of this synthetic potential, the substrate scope has not been fully investigated, probably owing to the difficulty of controlling the reactivity of transient thienyl anion species.…”

mentioning

confidence: 99%

“…We first examined the effects of substituents on the nitrogen atom of 2-iodoaniline derivatives for Negishi coupling using the 3,5-dibromothienyl lithium species, which was generated after the halogen dance of 2,5-dibromothiophene (Table ). In a previous report, halogen dance was performed with LDA at −78 °C. The resulting reaction mixture was treated with ZnCl 2 ·TMEDA at 0 °C, and the thienylzinc species that was generated in situ was subjected to the coupling conditions.…”

mentioning

confidence: 99%

Synthesis of Thieno[3,2-b]indoles via Halogen Dance and Ligand-Controlled One-Pot Sequential Coupling Reaction

2018

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A two-pot synthesis of thieno[3,2-b]indole from 2,5-dibromothiophene is described. A halogen dance of 2,5-dibromothiophene was performed with LDA, and subsequent Negishi coupling was performed with 2-iodoaniline derivatives to provide the corresponding coupling products. The resulting two bromo groups have different reactivities, which were utilized for the one-pot Suzuki-Miyaura coupling/intramolecular Buchwald-Hartwig amination to produce thieno[3,2-b]indole via an assisted tandem catalysis that involved in situ ligand exchange.

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Recent Advances in the Chemistry of Thiophenes

Cited by 99 publications

References 441 publications

Contact Angle and Electrochemical Characterization of Multicomponent Thiophene-Capped Monolayers

Contact Angle and Electrochemical Characterization of Multicomponent Thiophene-Capped Monolayers

Synthesis of Polysubstituted Ferrocenesulfoxides

Synthesis of Thieno[3,2-b]indoles via Halogen Dance and Ligand-Controlled One-Pot Sequential Coupling Reaction

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