A Simplified Synthesis of 3-Bromoselenophene and Some 3-Bromothiophenes

Hallberg, Anders; Liljefors, S.; Pedaja, P.

doi:10.1080/00397918108064278

Cited by 23 publications

(5 citation statements)

References 2 publications

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“…3-Bromo-2methylthiophene was prepared according to a literature procedure. 8 Tetrakis(triphenylphosphine)palladium(0) as a catalyst for Suzuki coupling was synthesized according to a literature procedure. 9 Tetrahydrofuran was distilled over sodium benzophenone ketyl before use.…”

Section: Methodsmentioning

confidence: 99%

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Syntheses, Luminescence Switching, and Electrochemical Studies of Photochromic Dithienyl-1,10-phenanthroline Zinc(II) Bis(thiolate) Complexes

Ngan

Zhu

et al. 2007

Inorg. Chem.

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A series of zinc(II) diimine bis(thiolate) complexes with photochromic diarylethene-containing phenanthroline ligands was synthesized, and their photophysical and photochromic properties were studied. The X-ray crystal structures of two of these complexes have been characterized. All complexes exhibit strong 3LLCT phosphorescence at 510-620 nm in the solid state at 77 and 298 K and in EtOH-MeOH glass at 77 K. Detailed studies revealed that the absorption, emission, and electrochemical properties of the complexes could be readily switched via the photochromic ring-closing and ring-opening reactions.

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Section: Methodsmentioning

confidence: 99%

“…Zinc acetate dihydrate was purchased from Merck Chemicals and recrystallized from water prior to use. 3-Bromo-2-methylthiophene was prepared according to a literature procedure …”

Section: Methodsmentioning

confidence: 99%

Syntheses, Luminescence Switching, and Electrochemical Studies of Photochromic Dithienyl-1,10-phenanthroline Zinc(II) Bis(thiolate) Complexes

Ngan

Zhu

et al. 2007

Inorg. Chem.

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“…It is known that 3-bromo- or 3-iodoselenophenes that cannot be obtained by direct monohalogenation of unsubstituted selenophene are obtained by reduction of 2,3,5-tribromoselenophene or 2,3,4,5-tetraiodoselenophene, respectively. Tellurium analogues are unknown, and reaction of unsubstituted tellurophene with bromine in methanol results in one product containing two bromine atoms bonded to the tellurium …”

Section: Resultsmentioning

confidence: 99%

Iodocyclization of (Z)-1-(Butyltelluro)-1,4-diorganylbut-1-en-3-ynes. Synthesis and Reactions of 3-Iodotellurophenes

Dabdoub

Pereira

et al. 1996

J. Org. Chem.

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The iodocyclization of (Z)-tellurobutenynes 5a − g by reaction with I2/petroleum ether was studied in detail. 3-Iodotellurophenes 7a − f were formed, and optimum conditions to obtain these compounds in high yields were established. The reaction involves attack of iodide at the initially formed intermediate of type 10 followed by ring closure that is favored by the strong aromatic character of the resulting products. Two possible and alternative pathways for the ring closure are proposed to explain our observations: (a) transformation of 10 to 11 that undergoes further cyclization to give 7a − f (pathway a) or (b) direct cyclization of 10 to give tellurophene diiodide 9 (pathway b). The products and side products obtained are in agreement with the proposed mechanisms. Formation of 7a from ditelluride 14 and iodine provides additional evidence of the intermediacy of 11 (in pathway a). Structures of 7a and 5g were elucidated by X-ray crystallography. In the case of compound 5e, where a terminal triple bond was present, the resulting intermediate of type 10 also underwent the attack of iodide directly at the terminal carbon to give compound 12 together with 7e. Ring-opening of 3-iodotellurophene 7a occurs by reaction with n-butyllithium to form acyclic ditelluride 14 or monotelluride 16 depending on the alkyllithium amounts employed. Plausible mechanisms for these novel reactions are proposed and supported. Conversion of 7a to 3-(butyltelluro)-2,5-diphenyltellurophene (22) was carried out readily by an unusual “aromatic nucleophilic substitution” using the butyl tellurolate anion.

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“…The reaction of selenophene with bromine affords a mixture of poly(bromo)selenophenes. Then, the addition of acetic acid and zinc dust to the reaction mixture promotes the selective debromination at C2 and C5 positions affording 3‐bromoselenophene in 47 % yield (Figure , top) . 3,4‐Dibromoselenophene can be prepared by treatment of tetrabromoselenophene by BuLi followed by hydrolysis (Figure , middle) .…”

Section: C3‐arylation Of Selenophenesmentioning

confidence: 99%

Access to (Hetero)arylated Selenophenes via Palladium‐catalysed Stille, Negishi or Suzuki Couplings or C−H Bond Functionalization Reaction

et al. 2017

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(Hetero)aryl‐substituted selenophenes exhibit important physical properties especially for optoelectronics. Palladium‐catalysed coupling reactions currently represent the most efficient methods to prepare such (hetero)arylated selenophene derivatives. Initially, Stille coupling was the most efficient reaction for the synthesis of these compounds; however, over the last decade, Suzuki coupling has become the most commonly employed. Recently, Pd‐catalysed arylation via the C−H bond activation of selenophenes has proved to be a very convenient alternative method for the preparation of several arylated selenophenes as there is no need to prepare organometallic derivatives. In this Review, the progress and substrate scope in the synthesis of both C2‐ and C3‐arylated selenophenes via Pd‐catalysis are summarized.

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A Simplified Synthesis of 3-Bromoselenophene and Some 3-Bromothiophenes

Cited by 23 publications

References 2 publications

Syntheses, Luminescence Switching, and Electrochemical Studies of Photochromic Dithienyl-1,10-phenanthroline Zinc(II) Bis(thiolate) Complexes

Syntheses, Luminescence Switching, and Electrochemical Studies of Photochromic Dithienyl-1,10-phenanthroline Zinc(II) Bis(thiolate) Complexes

Iodocyclization of (Z)-1-(Butyltelluro)-1,4-diorganylbut-1-en-3-ynes. Synthesis and Reactions of 3-Iodotellurophenes

Access to (Hetero)arylated Selenophenes via Palladium‐catalysed Stille, Negishi or Suzuki Couplings or C−H Bond Functionalization Reaction

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