16387-72-7Relevant academic research and scientific papers
A convenient synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via 1,3-dipolar cycloaddition/coupling of alkynes, phenylboronic acids, and sodium azide catalyzed by Cu(I)/Cu(II)
Yang, Dong,Fu, Na,Liu, Zenglu,Li, Ying,Chen, Baohua
, p. 278 - 282 (2007)
A series of 1,4,5-trisubstituted 1,2,3-triazoles was prepared simply and conveniently via 1,3-dipolar cycloaddition/coupling reaction of terminal alkynes, phenylboronic acids and sodium azide in 1,4-dioxane-water using CuI/CuSO4 as catalyst. Georg Thieme Verlag Stuttgart.
Cu–N-heterocyclic carbene-catalysed synthesis of 2-aryl-3-(arylethynyl)quinoxalines from one-pot tandem coupling of o-phenylenediamines and terminal alkynes
Motakatla, Venkata Krishna Reddy,Gokanapalli, Anusha,Peddiahgari, Vasu Govardhana Reddy
, (2019/09/03)
A series of new benzimidazolium chlorides bearing N,N′-benzyl, 2,4,6-trimethylbenzyl and 2,4,6-triisopropylbenzyl substituents have been designed and synthesized from various o-phenylenediamines. Subsequently, corresponding Cu-based N-heterocyclic carbenes (NHCs) were generated in situ in the reaction medium which represents a new application of NHCs exploiting distinct catalytic property towards intermolecular cyclization reaction cascade for the synthesis of 2-aryl-3-(arylethynyl)quinoxalines from o-phenylenediamines and terminal alkynes. The outcome of the cyclization reaction product depends upon the N,N′-substituents present on the benzimidazolium chlorides.
Copper(II)/Palladium(II) catalysed highly selective cross-coupling of terminal alkynes in supercritical carbon dioxide
Wang, Yunlong,Suo, Quanling,Han, Limin,Guo, Linlin,Wang, Yaqi,Li, Fawang
, p. 1918 - 1925 (2018/03/12)
An efficient protocol for the synthesis of unsymmetrical 1,3-diynes was developed using supercritical carbon dioxide (ScCO2) as the solvent. The direct coupling of two different terminal alkynes is catalysed by a bimetallic catalyst, CuCl2·2H2O/Pd(NH3)4Cl2·H2O, in the presence of the base tetramethylethylenediamine (TMEDA) and O2. In pure ScCO2, our bimetallic catalytic system maintains high activity over a wide substrate scope to provide unsymmetrical 1,3-diynes in good to excellent yields. In the proposed reaction mechanism, the synergistic cooperation between copper(II) and palladium(II) centres is responsible for the superior selectivity of the cross-coupling.
One-pot green synthesis of enamides and 1,3-diynes
Liang, Hao,Ren, Zhihui,Wang, Yaoyu,Guan, Zhenghui
, p. 113 - 118 (2015/09/28)
A green organic synthetic method combining reductive acylation of ketoximes and oxidative coupling of terminal alkynes was developed. This novel process enables enamides and 1,3-diynes to be synthesized simultaneously in high yields and under mild conditions without the use of terminal reductants/oxidants.
Copper-catalyzed cross-coupling of alkyl and aryl grignard reagents with alkynyl halides
Cahiez, Gerard,Gager, Olivier,Buendia, Julien
supporting information; experimental part, p. 1278 - 1281 (2010/05/18)
(Chemical Equation Presented) Good old copperl A new general procedure to couple aliphatic and aromatic Grignard reagents with alkynyl halides under copper catalysis is described (see scheme; NMP=N-methylpyrrolidinone). The reaction is chemoselective and allows preparation of a vast array of simple and functionalized internal alkynes in high yields.
Synthesis of cross-conjugated geminal enediynes via palladium catalyzed cross-coupling reaction of ketene butyltelluroacetals
Zeni, Gilson,Perin, Gelson,Cella, Rodrigo,Jacob, Raquel G.,Braga, Antonio L.,Silveira, Claudio C.,Stefani, Hélio A.
, p. 975 - 977 (2007/10/03)
The palladium-catalyzed cross coupling reaction of ketene butyltelluroacetals with terminal alkynes at room temperature affords cross-conjugated geminal enediynes in high yield under mild conditions.
PALLADIUM-MEDIATED REACTIONS BETWEEN 1-ALKYNYLZINC CHLORIDES AND (E)/(Z)-1,2-DIBROMOETHYLENE OR (E)-1,2-DIBROMO-1,2-DIPHENYLETHYLENE
Andreini, Bianca Patrizia,Benetti, Massimiliano,Carpita, Adriano,Rossi, Renzo
, p. 469 - 474 (2007/10/02)
A new synthetic method, i.e. the palladium-catalyzed diastereoselective alkynylation reaction of (E)/(Z)-1,2-dibromoethylene, 9, has been developed to conveniently prepare (E)-1-bromo-1-alken-3-ynes (12) and 1,6-di(hetero)aryl- or 1,6-dialkyl-substituted (E)-3-en-1,5-diynes (13) with very high stereoisomeric purity.Compounds 12 and 13 can be obtained selectively according to the molar ratio between the reagents.Evidence has been obtained that the diastereoselectivity of these alkynylation reactions can be attributed to a diastereoselective oxidative addition of (E)/(Z)-9 to the palladium(0) complex used as catalyst in these reactions.It has also been shown for the first time that the complexes which derive from the oxidative addition of (E)-9 or (E)-1,2-dibromo-1,2-diphenylethylene, 14, to Pd(PPh3)4 easily undergo decomposition affording both PdBr2(PPh3)2 and acetylene or diphenylacetylene, 19, respectively.Finally, it has been shown that the reaction of 14 with organozinc derivatives, in the presence of catalytic amounts of 11, affords diphenylacetylene, 19, selectively, instead of cross-coupling products.
