Synthesis of thiophene oligomers via organotin compounds

Samir A. Al-Taweel; Hassan F. Al-Saraierh

doi:10.1080/10426509908044969

Synthesis of thiophene oligomers via organotin compounds

Samir A. Al-Taweel
, Hassan F. Al-Saraierh

Preparatory Program

Mu'tah University

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes. Substituted bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 3-trimethylstannylthiophene. The latter reagent couples with bromoaromatics, bromoheteroaromatics and 2,5-dibromothiophenes to give the corresponding 3-arylthiophenes, 3-heteroarylthiophenes and terthiophenes, respectively. 2-Trimethylstannylthiophene couples with 2,5-dibromo-3-arylthi ophenes to give 3-aryl-α-terthiophenes. The structures of the new compounds were confirmed by elemental analysis, mass spectrometry, ¹H- and ¹³C-NMR spectral data.

Original language	British English
Pages (from-to)	47-57
Number of pages	11
Journal	Phosphorus, Sulfur and Silicon and Related Elements
Volume	155
DOIs	https://doi.org/10.1080/10426509908044969
State	Published - 1999

Keywords

3-trimethylstannylthiophene
3′-aryl-α-terthiophene
Functionalized bithiophene
Synthesis

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10.1080/10426509908044969

Cite this

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title = "Synthesis of thiophene oligomers via organotin compounds",

abstract = "A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes. Substituted bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 3-trimethylstannylthiophene. The latter reagent couples with bromoaromatics, bromoheteroaromatics and 2,5-dibromothiophenes to give the corresponding 3-arylthiophenes, 3-heteroarylthiophenes and terthiophenes, respectively. 2-Trimethylstannylthiophene couples with 2,5-dibromo-3-arylthi ophenes to give 3-aryl-α-terthiophenes. The structures of the new compounds were confirmed by elemental analysis, mass spectrometry, 1H- and 13C-NMR spectral data.",

keywords = "3-trimethylstannylthiophene, 3′-aryl-α-terthiophene, Functionalized bithiophene, Synthesis",

author = "Al-Taweel, \{Samir A.\} and Al-Saraierh, \{Hassan F.\}",

year = "1999",

doi = "10.1080/10426509908044969",

language = "British English",

volume = "155",

pages = "47--57",

journal = "Phosphorus, Sulfur and Silicon and Related Elements",

issn = "1042-6507",

publisher = "Taylor and Francis Ltd.",

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TY - JOUR

T1 - Synthesis of thiophene oligomers via organotin compounds

AU - Al-Taweel, Samir A.

AU - Al-Saraierh, Hassan F.

PY - 1999

Y1 - 1999

N2 - A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes. Substituted bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 3-trimethylstannylthiophene. The latter reagent couples with bromoaromatics, bromoheteroaromatics and 2,5-dibromothiophenes to give the corresponding 3-arylthiophenes, 3-heteroarylthiophenes and terthiophenes, respectively. 2-Trimethylstannylthiophene couples with 2,5-dibromo-3-arylthi ophenes to give 3-aryl-α-terthiophenes. The structures of the new compounds were confirmed by elemental analysis, mass spectrometry, 1H- and 13C-NMR spectral data.

AB - A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes. Substituted bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 3-trimethylstannylthiophene. The latter reagent couples with bromoaromatics, bromoheteroaromatics and 2,5-dibromothiophenes to give the corresponding 3-arylthiophenes, 3-heteroarylthiophenes and terthiophenes, respectively. 2-Trimethylstannylthiophene couples with 2,5-dibromo-3-arylthi ophenes to give 3-aryl-α-terthiophenes. The structures of the new compounds were confirmed by elemental analysis, mass spectrometry, 1H- and 13C-NMR spectral data.

KW - 3-trimethylstannylthiophene

KW - 3′-aryl-α-terthiophene

KW - Functionalized bithiophene

KW - Synthesis

UR - https://www.scopus.com/pages/publications/0033234214

U2 - 10.1080/10426509908044969

DO - 10.1080/10426509908044969

M3 - Article

AN - SCOPUS:0033234214

SN - 1042-6507

VL - 155

SP - 47

EP - 57

JO - Phosphorus, Sulfur and Silicon and Related Elements

JF - Phosphorus, Sulfur and Silicon and Related Elements

ER -

Synthesis of thiophene oligomers via organotin compounds

Abstract

Keywords

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