16387-71-6Relevant articles and documents
Ligand- and base-free synthesis of 1,3-diynes catalyzed by low loading of heterogeneous Pd/C and CuI
Kurita, Takanori,Abe, Masami,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
, p. 2521 - 2524 (2007)
A facile and environmentally friendly synthetic method for a variety of symmetrical 1,3-diyne derivatives based on the Pd/C-CuI-catalyzed homocoupling reaction of terminal alkynes has been developed. The reaction was efficiently catalyzed by the extremely
Pd-catalysed cross coupling of terminal alkynes to diynes in the absence of a stoichiometic additive
Fairlamb, Ian J. S.,Baeuerlein, Patrick S.,Marrison, Lester R.,Dickinson, Julia M.
, p. 632 - 633 (2003)
An efficient, room temperature procedure for the cross-coupling of a range of terminal alkynes, using standard Sonogashira cross-coupling conditions (Pd/Cu) is presented. At higher reaction temperatures, head-to-tail or head-to-head dimerisation affords 1,3- and 1,4-disubstituted enynes, respectively as minor products.
Synthesis of diynes by phase transfer catalysis in the presence of a Pd (0) catalyst
Vlassa,Ciocan-Tarta,Margineanu,Oprean
, p. 1337 - 1342 (1996)
A new method for diynes preparation by phase transfer catalysis in the presence of a Pd (0) catalyst is described.
Polymer-Supported Cu–Nanoparticle as an Efficient and Recyclable Catalyst for Oxidative Homocoupling of Terminal Alkynes
Aziz, Sk Tarik,Islam, Rafique Ul
, p. 205 - 213 (2018)
Abstract: Copper nanoparticle on polyaniline support was synthesised by using in situ polymerisation and composite formation technique. This metal polymer nanocomposites material is found to be efficient for homocoupling of terminal alkynes which afford s
CuI complexes with 2,2′-biquinolyl-containing polymeric ligands as electrocatalysts for the oxidative coupling of alkynes in the presence of dioxygen
Magdesieva,Dolganov,Yakimansky,Goikhman, M. Ya.,Podeshvo
, p. 2090 - 2092 (2008)
Electrocatalytic oxidative coupling of terminal alkynes in the presence of atmospheric oxygen catalyzed by CuI complexes with polymeric biquinolyl ligands leads to the corresponding diynes in high yield. The reaction proceeds under mild conditi
Synthesis of symmetrical 1,3-diynes via homocoupling reaction of n-butyl alkynyltellurides
Singh, Fateh V.,Amaral, M?nica F.Z.J.,Stefani, Hélio A.
, p. 2636 - 2639 (2009)
An ultrasound-assisted synthesis of symmetrical 1,3-diyne compounds with electron-withdrawing or -donating substituents is described and illustrated by the palladium-catalyzed homocoupling reaction of n-butyl alkynyltellurides. This procedure offers easy
Metallomicelle catalyzed aerobic tandem desilylation/Glaser reaction in water
Tang, Shanyu,Li, Longjia,Ren, Xuanhe,Li, Jiao,Yang, Guanyu,Li, Heng,Yuan, Bingxin
supporting information, p. 2899 - 2904 (2019/06/17)
PEG-grafted nitrogen ligands were synthesized. The corresponding copper complexes serve as metallomicellar nanoreactors for the aerobic tandem desilylation/Glaser coupling of TMS-protected alkynes in water. The protocol is also suitable for base-free homocoupling of terminal alkynes. The metallomicellar catalyst could be recycled 5 times with minor loss of reactivity.
Chemoselective Cobalt(I)-Catalyzed Cyclotrimerization of (Un)Symmetrical 1,3-Butadiynes for the Synthesis of 1,2,4-Regioisomers
Weber, Sebastian M.,Hilt, Gerhard
supporting information, p. 4106 - 4110 (2019/06/17)
The cobalt(I)-catalyzed cyclotrimerization of (un)symmetrical 1,4-disubstituted 1,3-butadiynes is presented. In the case of unsymmetrical 1,3-butadiynes, this reaction can generate eight 1,2,4-substituted and four 1,3,5-substituted isomers. A single 1,2,4-substituted isomer was formed in excellent yields (up to 99%) and exclusive regioselectivities (>99:1) when symmetrical or a 1,3-butadiyne with an aryl or alkyl substituent and a trimethylsilyl group were applied. A large number of products accepting a wide variety of functional groups were synthesized.
Synthesis of Aryl Alkynes via Copper Catalyzed Decarboxylative Alkynylation of 2-Nitrobenzoic Acids
Yu, Yongqi,Chen, Xiang,Wu, Qianlong,Liu, Da,Hu, Liang,Yu, Lin,Tan, Ze,Gui, Qingwen,Zhu, Gangguo
supporting information, p. 8556 - 8566 (2018/06/29)
An efficient protocol for the synthesis of internal aryl alkynes was achieved via Cu-catalyzed decarboxylative cross-coupling reactions, and to the best of our knowledge, this is the first example of a Cu-catalyzed decarboxylative alkynylation of benzoic acids with terminal alkynes. This approach utilizes simple Cu salt as catalyst and O2, an abundant, clean, and green material, as the oxidant. The reaction tolerates various functional groups, and a variety of internal aryl alkynes were synthesized in 46-83% yields.
Continuous-flow oxidative homocouplings without auxiliary substances: Exploiting a solid base catalyst
?tv?s, Sándor B.,Georgiádes, ádám,Mészáros, Rebeka,Kis, Koppány,Pálinkó, István,Fül?p, Ferenc
, p. 90 - 99 (2017/03/15)
The catalytic oxidative dimerization of aromatic amines and acetylenes is of outstanding synthetic importance among homocoupling reactions. Both transformations necessitate the use of extraneous bases and ligands, which contains significant disadvantages as concerns environmental impacts and process costs. We exploited the inherent basic character of a copper-containing layered double hydroxide to facilitate the catalytic homocouplings of alkynes and aniline derivatives without the need for any auxiliary substances. The reactions were studied in a continuous-flow system to achieve extended parameter spaces for chemical intensification, and also to avoid undesired reaction pathways by means of strategic control over the residence time. Valuable 1,4-disubstituted 1,3-diynes and diversely substituted aromatic azo compounds were achieved chemoselectively in excellent yields and in short process times even on preparative scales.
