30353-46-9Relevant academic research and scientific papers
Coupling of terminal alkynes promoted by organic polyvalent iodine compounds
Huang, Xian,Wang, Jun-Hua
, p. 9 - 14 (2000)
Terminal alkynes couple smoothly in the presence of PhI(OAc)2 or PhI(OH)OTs, catalytic amount of CuI and base, affording conjugated diynes.
Preparation of a Graphite-like Structured Polymer from 1-Phenylpenta-1,3-diyn-5-ol
Lee, Heung Jae,Shim, Sang Chul
, p. 1420 - 1422 (1993)
Poly(1-phenylpenta-1,3-diyn-5-ol) (PPDO), prepared by NbCl5/(Bun)4Sn catalysed metathesis of PDO, is converted into a graphite-like structure with a high conductivity in the absence of dopants by heat treatment at 800 degC under vacuum.
"clickable" thiacalix[4]arene derivatives bearing polymerizable 1,3-butadiyne fragments: Synthesis and incorporation into polydiacetylene vesicles
Burilov, Vladimir,Valiyakhmetova, Alsu,Mironova, Diana,Safiullin, Roman,Kadirov, Marsil,Ivshin, Kamil,Kataeva, Olga,Solovieva, Svetlana,Antipin, Igor
, p. 44873 - 44877 (2016)
p-tert-Butylthiacalix[4]arene derivatives in 1,3-alternate stereoisomeric form bearing polymerisable 1,3-butadiyne fragments on the one side and amino/carboxylic groups on another were synthesized using stepwise functionalisation. Calixarene 7 embedded in polydiacetylene nanoparticles showed a selective colorimetric response toward lanthanide ions.
A convenient route to unsymmetrical conjugated diynes
Alami, Mouad,Ferri, Fabiola
, p. 2763 - 2766 (1996)
Various unsymmetrical conjugated diynes can be prepared in good to excellent isolated yields by copper catalyzed coupling reaction of terminal alkynes with 1-iodo alkynes in pyrrolidine. In the case of 1-bromo alkynes, the presence of a catalytic amount o
A General and Highly Selective Palladium-Catalyzed Hydroamidation of 1,3-Diynes
Beller, Matthias,Franke, Robert,Jackstell, Ralf,Jiao, Haijun,Liu, Jiawang,Schneider, Carolin,Wei, Zhihong,Yang, Ji
supporting information, p. 371 - 379 (2020/10/29)
A chemo-, regio-, and stereoselective mono-hydroamidation of (un)symmetrical 1,3-diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α-alkynyl-α, β-unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density-functional theory (M06L-SMD) computations also suggest the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3-diynes.
In the optically-multiplexed-
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Paragraph 0216; 0217, (2020/12/30)
A method for optical super-multiplexing using polyynes to provide enhanced images from stimulated Raman microscopy is disclosed. In some exemplary embodiments, the polyynes are organelle-targeted or spectral barcoded. Imaging can be enhanced by using the polyynes to image whole live cells or specific organelles within live cells. The polyynes can also be used in optical data storage (i.e., encoding) and identification (i.e., decoding) applications.
Rh(III)-Catalyzed [3 + 2] Spirocyclization of 2 H-Imidazoles with 1,3-Diynes for the Synthesis of Spiro-[imidazole-indene] Derivatives
Luo, Yi,Liu, Hao,Zhang, Jing,Liu, Man,Dong, Lin
supporting information, p. 7604 - 7608 (2020/10/09)
An effective strategy to synthesize spirocyclic compounds, [imidazole-4,1′-indene], has been efficaciously developed relied on Rh(III)-catalyzed [3 + 2] spirocyclization of 2H-imidazoles and 1,3-diynes with excellent chemselectivity and regioselectivity.
Selective Hydroarylation of 1,3-Diynes Using a Dimeric Manganese Catalyst: Modular Synthesis of Z-Enynes
Yan, Zhongfei,Yuan, Xiang-Ai,Zhao, Yue,Zhu, Chengjian,Xie, Jin
supporting information, p. 12906 - 12910 (2018/09/25)
The transition-metal-catalyzed selective hydroarylation of unsymmetrical alkynes represents the state-of-art in organic chemistry, and still mainly relies on the use of precious late-transition-metal catalysts. Reported herein is an unprecedented MnI-catalyzed hydroarylation of unsymmetrical 1,3-diyne alcohols with commercially available arylboronic acids with predictive selectivity. This method addresses the challenges in regio-, stereo-, and chemoselectivity. It offers a general, convenient and practical strategy for the modular synthesis of multisubstituted Z-configurated conjugated enynes. This protocol is distinguished by its operational simplicity, complete selectivity, excellent functional-group compatibility, and gram-scale potential. A dimeric MnI species, Mn2(CO)8Br2, was proven to be a much more efficient catalyst precursor than Mn(CO)5Br.
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.
Glaser-Hay hetero-coupling in a bimetallic regime: A Ni(II)/Ag(i) assisted base, ligand and additive free route to selective unsymmetrical 1,3-diynes
Mohanty, Anuradha,Roy, Sujit
supporting information, p. 10796 - 10799 (2017/10/06)
A Ni(OAc)2/Ag(OTf) catalysed coupling of aryl alkynes and propargylic alcohol/ether/ester gave the corresponding unsymmetrical 1,3-diynes in good to excellent yields. The reaction does not require bases, ligands or additives and shows excellent hetero-selectivity, thereby addressing the current challenges in the field of coupling of two different terminal alkynes.
