29488-24-2Relevant articles and documents
Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates
Komatsuda, Masaaki,Kato, Hiroki,Muto, Kei,Yamaguchi, Junichiro
, p. 8991 - 8995 (2019)
A catalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbene species. T
Synthesis and properties of chromophore-functionalized monovinylsilsesquioxane derivatives
?ak, Patrycja,Bo?t, Ma?gorzata,Dudziec, Beata,Grzelak, Magdalena,Januszewski, Rafa?,Marciniak, Bronislaw,Marciniec, Bogdan,Rachuta, Karolina
, p. 7659 - 7664 (2020)
A facile and efficient Pd-based Suzuki-Miyaura coupling reaction leading to mixed chromophores with styryl fragments, enabling their further application, is presented. We also disclose their use in the formation of monofunctionalized silsesquioxanes with a chromophore group covalently bound to a T8 core that have been prepared via a cross-metathesis reaction. These new materials were studied in terms of their photophysical and also thermal properties.
ORGANIC COMPOUND, PRODUCTION METHOD OF THE SAME, ORGANIC LIQUID CRYSTAL, ORGANIC SEMICONDUCTOR AND THE LIKE
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Paragraph 0140; 0142, (2020/07/25)
PROBLEM TO BE SOLVED: To provide an organic semiconductor showing high mobility and high thermal stability and having excellent solubility, an organic compound for the organic semiconductor, and a production method of the compound. SOLUTION: The present invention discloses an organic compound represented by the formula (1) and a production method of the compound, and applications of an organic semiconductor and the like using the organic compound. In the formula, Ar is an aromatic group selected from a phenyl or a thienyl which may have a substituent; one of R1 and R2 is a linear aliphatic group and the other is a hydrogen atom; and an acetylene bond in the parenthesis may be present or absent. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
Decarboxylative Bromination of Heteroarenes: Initial Mechanistic Insights
Patel, Pritesh R.,Henderson, Scott H.,Roe, Mark S.,Honey, Mark A.
supporting information, p. 1603 - 1607 (2020/09/09)
After an initial report from our laboratory describing metal-free decarboxylative halogenation of various azaheteroarenes, we set out to investigate the possible mechanism by which this chemistry occurs. Evidence from this mechanistic investigation sugges
A Rational Design of Highly Controlled Suzuki-Miyaura Catalyst-Transfer Polycondensation for Precision Synthesis of Polythiophenes and Their Block Copolymers: Marriage of Palladacycle Precatalysts with MIDA-Boronates
Seo, Kyeong-Bae,Lee, In-Hwan,Lee, Jaeho,Choi, Inho,Choi, Tae-Lim
, p. 4335 - 4343 (2018/04/05)
Herein, we report a highly efficient Suzuki-Miyaura catalyst-transfer polycondensation (SCTP) of 3-alkylthiophenes using bench-stable but highly active Buchwald dialkylbiarylphospine Pd G3 precatalysts and N-methylimidodiacetic (MIDA)-boronate monomers. Initially, the feasibility of the catalyst-transfer process was examined by screening various dialkylbiarylphospine-Pd(0) species. After optimizing a small molecule model reaction, we identified both RuPhos and SPhos Pd G3 precatalysts as excellent catalyst systems for this purpose. On the basis of these model studies, SCTP was tested using either RuPhos or SPhos Pd G3 precatalyst, and 5-bromo-4-n-hexylthien-2-yl-pinacol-boronate. Poly(3-hexylthiophene) (P3HT) was produced with controlled molecular weight and narrow dispersity for a low degree of polymerization (DP) only, while attempts to synthesize P3HT having a higher DP with good control were unsuccessful. To improve the control, slowly hydrolyzed 5-bromo-4-n-hexylthien-2-yl-MIDA-boronate was introduced as a new monomer. As a result, P3HT and P3EHT (up to 17.6 kg/mol) were prepared with excellent control, narrow dispersity, and excellent yield (>90%). Detailed mechanistic investigation using 31P NMR and MALDI-TOF spectroscopy revealed that both fast initiation using Buchwald precatalysts and the suppression of protodeboronation due to the protected MIDA-boronate were crucial to achieve successful living polymerization of P3HT. In addition, a block copolymer of P3HT-b-P3EHT was prepared via SCTP by sequential addition of each MIDA-boronate monomer. Furthermore, the same block copolymer was synthesized by one-shot copolymerization for the first time by using fast propagating pinacol-boronate and slow propagating MIDA-boronate.
Thiophene-S, S -dioxidized diarylethenes for light-starting irreversible thermosensors that can detect a rise in heat at low temperature
Kitagawa, Daichi,Tanaka, Koki,Kobatake, Seiya
, p. 6210 - 6215 (2017/07/11)
Diarylethenes having trimethylsilyl and triethylsilyl groups at the reactive positions and their S,S-dioxidized diarylethenes were synthesized and their optical and thermal properties were investigated. Upon irradiation with ultraviolet light, the diarylethenes and thiophene-S,S-dioxidized diarylethenes underwent photochromic reactions from the colourless open-ring isomer to the coloured closed-ring isomer. The photogenerated closed-ring isomers were found to undergo thermal bleaching reactions to produce colourless byproducts. In particular, the thiophene-S,S-dioxidized diarylethene having a triethylsilyl group at the reactive positions underwent the thermal bleaching reaction even at -40 °C. Such materials could be used as light-starting irreversible thermosensors that can detect a rise in heat at low temperature.
Thiophene-Alkyne-Based CMPs as Highly Selective Regulators for Oxidative Heck Reaction
Li, Ren-Hao,Ding, Zong-Cang,Li, Cun-Yao,Chen, Jun-Jia,Zhou, Yun-Bing,An, Xiao-Ming,Ding, Yun-Jie,Zhan, Zhuang-Ping
supporting information, p. 4432 - 4435 (2017/09/11)
Thiophenes containing an adjacent C≡C group as ligands for PdII-promoted organic reactions are reported for the first time. These ligands were utilized as catalytic sites and integrated into the skeleton of conjugated microporous polymers. By e
Structural requirements for palladium catalyst transfer on a carbon-carbon double bond
Nojima, Masataka,Ohta, Yoshihiro,Yokozawa, Tsutomu
supporting information, p. 5682 - 5685 (2015/05/20)
Intramolecular transfer of tBu3PPd(0) on a carbon-carbon double bond (C=C) was investigated by using Suzuki-Miyaura coupling reaction of dibromostilbenes with aryl boronic acid or boronic acid esters in the presence of various additi
Acid-base-responsive intense charge-transfer emission in donor-acceptor-conjugated fluorophores
Inouchi, Toshifumi,Nakashima, Takuya,Kawai, Tsuyoshi
supporting information, p. 2542 - 2547 (2014/10/15)
Herein we report on the synthesis and acid-responsive emission properties of donor-acceptor (D-A) molecules that contain a thienothiophene unit. 2-Arylthieno[3,2-b]thiophenes were conjugated with an N-methylbenzimidazole unit to form acid-responsive D-A-t
Gold-catalyzed oxidative coupling of arylsilanes and arenes: Origin of selectivity and improved precatalyst
Ball, Liam T.,Lloyd-Jones, Guy C.,Russell, Christopher A.
supporting information, p. 254 - 264 (2014/01/23)
The mechanism of gold-catalyzed coupling of arenes with aryltrimethylsilanes has been investigated, employing an improved precatalyst (thtAuBr3) to facilitate kinetic analysis. In combination with linear free-energy relationships, kinetic isotope effects, and stoichiometric experiments, the data support a mechanism involving an Au(I)/Au(III) redox cycle in which sequential electrophilic aromatic substitution of the arylsilane and the arene by Au(III) precedes product-forming reductive elimination and subsequent cycle-closing reoxidation of the metal. Despite the fundamental mechanistic similarities between the two auration events, high selectivity is observed for heterocoupling (C-Si then C-H auration) over homocoupling of either the arylsilane or the arene (C-Si then C-Si, or C-H then C-H auration); this chemoselectivity originates from differences in the product-determining elementary steps of each electrophilic substitution. The turnover-limiting step of the reaction involves associative substitution en route to an arene π-complex. The ramifications of this insight for implementation of the methodology are discussed.
