33589-44-5Relevant academic research and scientific papers
CuII-Catalyzed Oxidative Formation of 5-Alkynyltriazoles
Liu, Peiye,Brassard, Christopher J.,Lee, Justin P.,Zhu, Lei
, p. 380 - 390 (2020/01/24)
In an alcoholic solvent under the catalysis of Cu(OAc)2?H2O, organic azide and terminal alkyne could oxidatively couple to afford 5-alkynyl-1,2,3-triazole (alkynyltriazole) at room temperature under an atmosphere of O2 in a few hours. The involvement of 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) is essential, without which the redox neutral coupling instead proceeds to produce 5-H-1,2,3-triazole (protiotriazole) as the major product. Therefore, DBN switches the redox neutral coupling between terminal alkyne and organic azide, the copper-catalyzed “click” reaction to afford protiotriazole, to an oxidation reaction that results in alkynyltriazole. The organic base DBN is effective in accelerating the copper(II)-catalyzed oxidation of terminal alkyne or copper(I) acetylide, which is intercepted by an organic azide to produce alkynyltriazole. The proposed mechanistic model suggests that the selectivity between alkynyl- and protiotriazole, and other acetylide or triazolide oxidation products is determined by the competition between copper(I)-catalyzed redox neutral cycloaddition and copper(II)/O2-mediated acetylide oxidation after the formation of copper(I) acetylide.
Facile Preparation of Organometallic Nanorods from Various Ethynyl-Substituted Molecules
Nishijo, Junichi,Akashi, Takaaki,Enomoto, Masaya,Akita, Motoko
, p. 873 - 878 (2019/08/06)
A facile method to prepare one-dimensional (1D) organometallic nanomaterials from various ethynyl-substituted molecules is reported. The reactions of 3-chloro-1-ethynylbenzene, p-tBu-phenylacetylene and 4-ethynylbiphenyl with Cu+ ions in aceton
Ligand-Free Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Oxidative Homo-Coupling of Alkenyllithiums
Zhong, Zhuliang,Wang, Zhi-Yong,Ni, Shao-Fei,Dang, Li,Lee, Hung Kay,Peng, Xiao-Shui,Wong, Henry N. C.
supporting information, p. 700 - 704 (2019/02/07)
A new strategy was developed for the efficient synthesis of di-, tetra-, and hexa-substituted 1,3-butadienes. This one-pot procedure involves lithium-iodine exchange to generate the corresponding vinyllithium intermediates. A subsequent iron-catalyzed ligand-free oxidative homo-coupling eventually led to the formation of 1,3-butadienes in acceptable to excellent isolated yields.
External oxidant-free cross-coupling of arylcopper and alkynylcopper reagents leading to arylalkyne
Wang, Sheng,Min, Yaosen,Zhang, Xiaowei,Xi, Chanjuan
, p. 28308 - 28312 (2017/07/07)
External oxidant-free oxidative cross-coupling between arylcopper and alkynylcopper has been performed, which provides a new way for the formation of arylalkyne with high selectivity.
Direct Metal-Free Entry to Aminocyclobutenes or Aminocyclobutenols from Ynamides: Synthetic Applications
Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos
supporting information, p. 8998 - 9005 (2016/07/06)
The [2+2] cycloaddition of ynamides with the highly polarized reagent Tf2C=CH2has been developed to regioselectively afford bis(triflyl)aminocyclobutenes in the absence of catalyst under mild conditions. Incidentally, with the ynamides bearing electron-rich aromatic rings at the C-terminal, an interesting reactivity switch was observed; a cyclization/hydroxylation sequence yielded 2-amino-3-(triflyl)cyclobut-2-enols. Aminocyclobutene construction with addition of alcohols resulted in the formation of aminocyclobutenyl ethers through a cyclization/hydroalkoxylation process. Moreover, the utility of functionalized aminocyclobutenes as precursors for further elaboration was demonstrated with the preparation of α-amino-β,γ-unsaturated ketones and 3-(triflyl)buta-1,3-dien-2-amines through 4 π-electrocyclic ring opening.
Triplet-state benzophenone-sensitied photoreduction of bis(acetylacetonato)copper(II): the generation and stability of copper(I) complexes
Chow, Yuan L.,Buono-Core, Gonzalo E.
, p. 795 - 800 (2007/10/02)
Triplet-state benzophenone rapidly sensitized the photoreduction of Cu(acac)2 in alcohols to give polymeric Cu(acac) as black precipitates.The binary complexes of Cu(acac) of polypyridines, polysulfide, olefins, acetylenes, and carbon monoxide could be generated in solution under an inert atmosphere when a ligand was present in situ during photoreduction or added after an appropriate photoreduction was completed.Except Cu(acac)-(PPh3)2, the Cu(acac) complexes of various ligands are sensitive to air oxidation, but show a wide range of reactivity towards disproportionation and photolysis.In the presence of terminal acetylenes, amorphous copper(I) acetylides were isolated in good yields.
