99698-10-9Relevant academic research and scientific papers
Synthesis of Unsymmetric Monosubstituted and Disubstituted Dinaphthothiophenes
Throgmorton, John C.,Chintala, Satyanarayana M.,McCulla, Ryan D.
supporting information, p. 3682 - 3688 (2017/10/09)
Dinaphthothiophenes (DNTs) are a class of compounds with potential uses in organic semiconductors and the synthesis of unsymmetric catalysts. Symmetrical or asymmetrical addition of functional groups to the DNT structure may be desired for steric bulk in binaphthyl catalyst synthesis or tuning the electronic properties of semiconductors. Thus, versatility of functional group addition is a great asset in DNT synthesis. Until now, no versatile and concise methods for the synthesis of unsymmetrically substituted DNTs have been reported. Herein, we report three synthetic routes for the creation of three different classes of DNTs. Each route involves the successive addition of two functionalized styryl groups to a thiophene ring, followed by a photocyclization to form the desired asymmetric DNT. Various novel unsymmetrically monosubstituted and disubstituted dinaphtho[2,1-b:1′,2′-d]thiophenes, dinaphtho[1,2-b:1′,2′-d]thiophenes, and dinaphtho[1,2-b:2′,1′-d]thiophenes were synthesized from 2-bromothiophene,2,4-dibromothiophene, and 3,4-dibromothiophene in three or four steps. These methods can be used to synthesize a wide variety of unsymmetrically functionalized DNTs.
Benzyllithiums bearing aldehyde carbonyl groups. A flash chemistry approach
Nagaki, Aiichiro,Tsuchihashi, Yuta,Haraki, Suguru,Yoshida, Jun-ichi
supporting information, p. 7140 - 7145 (2015/07/01)
Reductive lithiation of benzyl halides bearing aldehyde carbonyl groups followed by reaction with subsequently added electrophiles was successfully accomplished without affecting the carbonyl groups by taking advantage of short residence times in flow microreactors.
Harnessing "click"-type chemistry for the preparation of novel electronic materials
Firstenberg, Michal,Shivananda, Kammasandra Nanjunda,Cohen, Irit,Solomeshch, Olga,Medvedev, Vladislav,Tessler, Nir,Eichen, Yoav
experimental part, p. 634 - 643 (2012/01/12)
Sequence-independent or "click"-type chemistry is applied for the preparation of novel π-conjugated oligomers. A variety of bi-functional monomers for Wittig-Horner olefination are developed and applied in a sequential protection-deprotection process for the preparation of structurally similar π-conjugated oligomers. Selected oligomers are incorporated as the organic semiconductors in light-emitting diodes and a field-effect transistor, demonstrating the potential of the approach. Sequence-independent or "click"-type chemistry is applied for the preparation of novel π-conjugated oligomers. A variety of bi-functional monomers for Wittig-Horner olefination are developed and applied in a sequential protection-deprotection process for the preparation of structurally similar π-conjugated oligomers. Selected oligomers are incorporated as the organic semiconductors in light-emitting diodes and a field-effect transistor, demonstrating the potential of the approach.
Palladium-catalyzed cross-coupling reactions of potassium alkenyltrifluoroborates with organic halides in aqueous media
Alacid, Emilio,Najera, Carmen
supporting information; experimental part, p. 2321 - 2327 (2009/07/18)
Potassium vinyl and alkenyltrifluoroborates are cross-coupled with aryl and heteroaryl bromides using 1 mol % Pd loading of 4-hydroxyacetophenone oxime derived palladacycle or Pd(OAc)2 as precatalysts, K 2CO3 as base, and TBAB as additive and water reflux under conventional or microwave heating to afford styrenes, stilbenoids, and alkenylbenzenes. These borates can be cross-coupled diastereoselectively with allyl and benzyl chlorides using KOH as base in acetone-water (3:2) at 50°C and 0.1 mol % Pd loading, giving the corresponding 1,4-dienes and allylarenes, respectively. These simple phosphine-free reaction conditions allow the palladium recycling from the aqueous phase during up to five runs by extractive separation of the products, which contain 58-105 ppm of Pd.
General reaction conditions for the palladium-catalyzed vinylation of aryl chlorides with potassium alkenyltrifluoroborates
Alacid, Emilio,Najera, Carmen
supporting information; experimental part, p. 8191 - 8195 (2010/03/04)
(Chemical Equation Presented) Activated and deactivated aryl and heteroaryl chlorides are efficiently cross-coupled with potassium vinyl- and alkenyltrifluoroborates using 4-hydroxyacetophenone oxime derived palladacycle as precatalyst in 1 to 3 mol % Pd loading, Binap as ligand, and Cs 2CO3 as base in DMF at 120°C. The reactions can also be performed using Pd(OAc)2 as Pd(0) source, although with lower efficiency. Bidentate ligands such as Binap and dppp can be used, the former being the best choice. Only in the case of deactivated aryl chlorides should the reaction temperature be increased to 160°C to achieve good yields. The corresponding cross-coupled compounds, such as styrenes, stilbenes, and alkenylarenes, are obtained in good yields and with high regio- and diastereoselectivity. 2009 American Chemical Society.
Heck reaction with heteroaryl halides in the presence of a palladium-tetraphosphine catalyst
Berthiol, Florian,Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
, p. 5625 - 5628 (2007/10/03)
cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/1/2[PdCl (C3H5)]2 system catalyses efficiently the Heck reaction of heteroaryl halides with n-butyl acrylate, styrene, vinylpyridine and vinyl ether derivatives. High turnover numbers can be obtained for the reactions with halo pyridines, quinolines, furans or thiophenes.
SYNTHESIS OF (5-STYRYL-2-THIENYL)-PHENYLACRYLIC ACIDS
Karminski-Zamola, Grace,Bajic, Miro
, p. 1497 - 1501 (2007/10/02)
We describe the synthesis of E-3-(5-styryl-2-thienyl)-2-phenylacrylic acid 7, E-3-(5-styryl-2-thienyl)-2-(4-methoxyphenyl)acrylic acid 8, E-3--2-phenylacrylic acid 9 and E-3--2-(4
