170859-75-3Relevant academic research and scientific papers
Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes
Shan, Qi-Chao,Hu, Lu-Min,Qin, Wei,Hu, Xu-Hong
supporting information, p. 6041 - 6045 (2021/08/03)
Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.
Bi(OTf)3-catalyed One-pot Synthesis of α-Halo-β-amino Ketones and Acyl Aziridines from 3-Aryl Propargyl Alcohols
Zhang, Qinglin,Duan, Yongbin,Guo, Huifeng,Yang, Hong,Zhai, Jiulong,Li, Tiantian,Wang, Zhihai,Lu, Xiaolei,Wang, Yan,Yin, Yan
supporting information, p. 1832 - 1838 (2021/06/09)
A Bi(OTf)3-catalyed reaction of 3-aryl propargyl alcohols with sulfonamide and halogen source was firstly investigated, which provided a facile route for the synthesis of a large variety of α-halo-β-amino ketones. The key intermediates, β-amino
3-aryl-2-propyn-1-ol derivative and preparation method thereof
-
Paragraph 0121-0133, (2020/12/31)
The invention discloses a 3-aryl-2-propyn-1-ol derivative and a preparation method thereof, belongs to the field of organic synthesis, and particularly relates to a 3-aryl-2-propyn-1-ol derivative anda preparation method thereof. A purpose of the invention is to solve the problems of high energy consumption, high cost and environmental pollution caused by conditions of high temperature, metal catalysis, strong base or low temperature and the like required by the synthesis of the existing 3-aryl-2-propyn-1-ol derivative. The structural formula of the 3-aryl-2-propyn-1-ol derivative is shown inthe specification. The method comprises the following steps: 1, sequentially adding an aryl acetylene compound, an ammonium salt, an alkali, water and an organic solvent into a three-necked flask, and electrolyzing at room temperature in an air atmosphere under a stirring condition; 2, extracting, and carrying out reduced pressure distillation to remove the solvent to obtain a crude product; and3, purifying the crude product through silica gel column chromatography to obtain the 3-aryl-2-propyn-1-ol derivative. According to the invention, the 3-aryl-2-propyn-1-ol derivative can be obtained.
Fine-tuning the solid-state ordering and thermoelectric performance of regioregular P3HT analogues by sequential oxygen-substitution of carbon atoms along the alkyl side chains
Chen, Liangjun,Liu, Wei,Yan, Yonggao,Su, Xianli,Xiao, Shengqiang,Lu, Xinhui,Uher, Ctirad,Tang, Xinfeng
, p. 2333 - 2344 (2019/03/05)
Conjugated polymers in thin films tend to orient their backbones with respect to substrates through self-assembly when processed from a solution. The molecular packing orientation and crystallinity of polymer crystals have been found to play a critical role in terms of their electrical performance. Taking advantage of the shorter bond length and the smaller rotation energy of the CH2-O bond than those of the CH2-CH2 bond in an alkyl chain, a side-chain engineering strategy is reported, which involves sequential oxygen-substitution of the carbon atoms from the γ position outwards along the hexyls in regioregular poly(3-hexylthiophene) (RR-P3HT). The subtle disparity between the CH2-O and CH2-CH2 bonds is found to enable fine tuning of the solid-state organization of the corresponding RR-P3HT analogues, namely poly(3-(2-propoxyethyl)thiophene) (P3POET), poly(3-(3-ethoxypropyl)thiophene) (P3EOPT) and poly(3-(4-methoxybutyl)thiophene) (P3MOBT). The evolution of film microstructures is observed when doping with FeCl3 in nitromethane at room temperature, and so is their thermoelectric performance. The highest power factor of 19 μW m-1 K-2 was observed for the doped P3POET film, which presents a dominant edge-on orientation with the strongest crystallinity and the closest π-π stacking. At the doping time corresponding to the optimized power factors (PFs) for each polymer, the doped P3POET film maintains both relatively high Seebeck coefficient (S) and electrical conductivity (σ) close to their maximum values, while the other polymers show either higher S and much lower σ (P3HT) or higher σ but much lower S (P3EOPT and P3MOBT). The square dependence of the PFs on S together with higher σ amplifies the power factor value of P3POET, which is almost 2 times those of the other polymers (11-13 μW m-1 K-2).
Bi(OTf)3 catalyzed synthesis of acyclic β-sulfanyl ketones via a tandem Meyer-Schuster rearrangement/conjugate addition reaction
Wang, Yuan,Yin, Yan,Zhang, Qinglin,Pan, Wanyong,Guo, Huifeng,Pei, Keke
supporting information, p. 2030 - 2034 (2019/07/03)
A new strategy to prepare acyclic β-carbonyl thioethers from propargyl alcohols and sulfur nucleophiles is reported. The investigation of the reaction substrates scope indicated that primary 3-aryl propargyl alcohols and thiols underwent the transformation smoothly. The reaction probably proceeded a Bi(OTf)3-catalyzed tandem Meyer-Schuster rearrangement of 3-aryl propargyl alcohol, followed by a thiol Michael conjugate addition of thiols to in situ generated α, β-unsaturated ketones. The method was 100% atom economic, high-yielding, and easy to handle, making it a valuable method for the construction of β-carbonyl sulfides.
Cobalt-catalyzed (Z)-selective semihydrogenation of alkynes with molecular hydrogen
Chen, Caiyou,Huang, Yi,Zhang, Zongpeng,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 4612 - 4615 (2017/04/28)
Cobalt-catalyzed highly (Z)-selective semihydrogenation of alkynes using molecular H2 was developed using commercially available and cheap cobalt precursors. A variety of (Z)-alkenes were obtained in moderate to excellent selectivities [(Z)-alkene/(E)-alkene/alkane ratio up to >99 : 1 : 1] and it was found that the readily available ethylenediamine ligand is crucial in determining the selectivity.
Construction of Condensed Polycyclic Aromatic Frameworks through Intramolecular Cycloaddition Reactions Involving Arynes Bearing an Internal Alkyne Moiety
Yoshida, Suguru,Shimizu, Keita,Uchida, Keisuke,Hazama, Yuki,Igawa, Kazunobu,Tomooka, Katsuhiko,Hosoya, Takamitsu
supporting information, p. 15332 - 15335 (2017/10/18)
Facile synthetic methods for condensed polycyclic aromatic compounds via aryne intermediates are reported. The generation of arynes bearing a (3-arylpropargyl)oxy group from the corresponding o-iodoaryl triflate-type precursors efficiently afforded arene-fused oxaacenaphthene derivatives, which were formed through intramolecular [2+4] cycloaddition. Extending the method to the generation of arynes bearing a 1,3-diyne moiety led to a continuous generation of naphthalyne intermediate through the hexadehydro Diels–Alder reaction involving the aryne triple bond. This novel type of aryne-relay chemistry enabled the synthesis of a unique aminoarylated oxaacenaphthene derivative and highly ring-fused anthracene derivatives.
Sodium Phenoxide Mediated Hydroxymethylation of Alkynylsilanes with N-[(Trimethylsiloxy)methyl]phthalimide
Asano, Narumi,Sasaki, Keita,Chataigner, Isabelle,Shigeno, Masanori,Kondo, Yoshinori
supporting information, p. 6926 - 6930 (2017/12/26)
The hydroxymethylation of alkynylsilanes with formaldehyde generated in situ from N-[(trimethylsiloxy)methyl]phthalimide proceeds in the presence of a stoichiometric amount of NaOPh. The reaction occurs at room temperature by using an operationally simple one-step procedure. A variety of alkynylsilanes possessing electron-donating, electron-withdrawing, and halogen groups (including heteroaryl-substituted alkynylsilanes) provide hydroxymethylated products.
Fe(OTf)3-catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones
Tao, Ruiheng,Yin, Yan,Duan, Yongbin,Sun, Yuxing,Sun, Yue,Cheng, Fengkai,Pan, Jinpeng,Lu, Cheng,Wang, Yuan
, p. 1762 - 1768 (2017/03/08)
Fe(OTf)3-catalyzed synthesis of acyclic β-aminoketones from 3-aryl propargyl alcohols and nitrogen nucleophiles were investigated. Results showed that propargyl alcohols without bulky groups α to the hydroxyl group underwent the transformation smoothly. Sulphonamides exhibited the higher reactivity than amides as the nitrogen nucleophiles and the transformation of acyclic β-aminoketones were finished in shorter reaction time and higher yields. Finally, racemic fluoxetine was efficiently accessed with the present reaction as the first step. This novel synthesis of acyclic β-aminoketones probable proceeded a Fe(OTf)3-catalyzed Meyer-Schuster rearrangement of 3-aryl propargyl alcohols, followed by a intermolecular hydroamination between nitrogen nucleophiles and α, β-unsaturated ketones.
An approach to the selenobromination of aryl(thienyl)alkynes: Access to 3-bromobenzo[b]selenophenes and selenophenothiophenes
Paegle, Edgars,Belyakov, Sergey,Arsenyan, Pavel
supporting information, p. 3831 - 3840 (2014/06/24)
A novel approach for the cyclization of arylalkynes with selenium(IV) bromide prepared in situ has been elaborated. The use of an alkene additive as a bromine scavenger provides a convenient synthetic pathway for the synthesis of a wide variety of 3-bromobenzo[b]selenophenes. Reactions can be performed open to air without the use of moisture-sensitive reagents, anhydrous solvents, or an inert atmosphere. Selenobromination of ethynylthiophenes has been applied for the preparation of selenopheno[3,2-b]- and selenopheno[2,3-b]thiophenes. The molecular structures of representative derivatives have been confirmed by X-ray crystallographic analysis. The use of an alkene additive as a bromine scavenger under selenobromination conditions provides a convenient synthetic pathway for the synthesis of a wide variety of 3-bromobenzo[b]selenophenes in moderate to high yields. The reactions are not moisture-sensitive and do not require an inert atmosphere. Selenobromination of ethynylthiophenes enables the preparation of selenopheno[b]thiophenes. Copyright
