1120-29-2Relevant articles and documents
Formal Gold-to-Gold Transmetalation of an Alkynyl Group Mediated by Palladium: A Bisalkynyl Gold Complex as a Ligand to Palladium
Toledo, Alberto,Meana, Isabel,Albéniz, Ana C.
supporting information, p. 13216 - 13220 (2015/09/15)
The reaction of [Au(C-C n-Bu)]n with [Pd(η3-allyl)Cl(PPh3)] results in a ligand and alkynyl rearrangement, and leads to the heterometallic complex [Pd(η3-allyl){Au(C-C n-Bu)2}]2 (3) with an unprecedented bridging bisalkynyl-gold ligand coordinated to palladium. This is a formal gold-to-gold transmetalation that occurs through reversible alkynyl transmetalations between gold and palladium. Back and forth! Direct gold-to-palladium and reverse palladium-to-gold alkynyl transmetalations effectively produce a deceptively simple gold-to-gold transfer. The resulting bisalkynyl-gold complexes act as bridging ligands to palladium atoms in an unprecedented structural motive (see scheme).
Facile synthesis of 3, 3′-disubstituted 2, 2′-binaphthyls by transition-metal-catalyzed double benzannulation
Umeda, Rui,Tabata, Hiromasa,Tobe, Yoshito,Nishiyama, Yutaka
supporting information, p. 883 - 884 (2014/06/23)
3, 3′-Disubstituted 2, 2′-binaphthyls were prepared by the Cuor Re-catalyzed double benzannulation reaction of 2-(phenylethynyl) benzaldehyde with various butadiynes in the presence of trichloroacetic acid, in moderate to good yields. Acceleration of the second benzannulation was clearly observed.
Heterometallic complexes by transmetalation of alkynyl groups from copper or silver to allyl palladium complexes: Demetalation studies and alkynyl homocoupling
Meana, Isabel,Espinet, Pablo,Albeniz, Ana C.
supporting information, p. 1 - 7 (2014/02/14)
The reaction of [Pd(η3-allyl)ClL] (L = AsPh3, PPh3) with [M(Ci - CR)]n (M = Cu, Ag; R = nBu, Ph) leads to transmetalation of the alkynyl group from M to Pd. However, the group 11 metal stays η2-bound to the new Pd-alkynyl fragment and heterometallic Pd-M complexes are formed with different nuclearities depending on M: [{Pd(η3-allyl)(alkynyl)L}CuCl] 2 (3, 4) or [{Pd(η3-allyl)(alkynyl)L}2AgCl] (5, 6). The M-containing fragment can be eliminated to give the actual transmetalation complex [Pd(η3-allyl)(alkynyl)L] by adding an excess of arsine or phosphine, whereas amines do not have this effect. Allyl-alkynyl reductive elimination is a slow process; therefore, complexes 3-6 cleanly decompose by dimerization (homocoupling) of the alkynyl group. In the decomposition process reversible alkynyl transmetalation from Pd to Cu has been observed.
Synthesis of unsymmetrical 1,3-diynes via alkyne cross-metathesis
Li, Sin Ting,Schnabel, Tobias,Lysenko, Sergej,Brandhorst, Kai,Tamm, Matthias
supporting information, p. 7189 - 7191 (2013/08/15)
The tungsten benzylidyne complex [PhC≡W{OSi(OtBu)3} 3] (1) efficiently catalyses the metathetic conversion between symmetrical and unsymmetrical 1,3-diynes, which provides the opportunity to prepare the latter species directly from terminal alkynes by a combination of copper-catalysed homocoupling and catalytic alkyne cross-metathesis (ACM).
Palladium-catalyzed acylation and/or homo-coupling of aryl- and alkyl-acetylenes
Perrone, Serena,Bona, Fabio,Troisi, Luigino
experimental part, p. 7386 - 7391 (2011/10/09)
Allyl or benzyl halides, through a Pd(0)-catalyzed reaction and under CO pressure, generate acyl-palladium/halides that, in the presence of a base and an aryl- and alkyl-acetylene, undergo nucleophilic acyl substitution giving conjugated acetylenic ketones. Diynes, resulting from alkyne/alkyne homo-coupling, were instead the main products in reactions performed without allyl or benzyl halides. Moreover, dimerization, trimerization, and cyclotrimerization reactions of acetylenes were observed in reaction carried out even without base.
Iron/copper promoted oxidative homo-coupling reaction of terminal alkynes using air as the oxidant
Meng, Xu,Li, Chuanbin,Han, Baochun,Wang, Tiansheng,Chen, Baohua
supporting information; scheme or table, p. 4029 - 4031 (2010/07/06)
An inexpensive catalytic system, which used a readily available Fe(acac)3 and trace quantity of Cu(acac)2 as the co-catalyst and air as the oxidant for the homo-coupling of terminal alkynes, has been developed. The catalytic system could also apply to the cross-coupling reaction of two different terminal alkynes.
Cobalt-catalyzed benzyl-alkynyl coupling
Kuno, Akiko,Saino, Naoko,Kamachi, Taku,Okamoto, Sentaro
, p. 2591 - 2594 (2007/10/03)
Benzylic halides coupled with 1-alkynylmagnesium halides in the presence of a catalytic amount of Co(acac)3 to provide 1-aryl-2-alkynes in moderate to good yield.
Potassium organotrifluoroborates: New partners in palladium-catalysed cross-coupling reactions
Darses, Sylvain,Michaud, Guillaume,Genet, Jean-Pierre
, p. 1875 - 1883 (2007/10/03)
The preparation of various potassium organotrifluoroborates bearing either aryl, alkenyl, or alkynyl substituents is described. These stable salts are shown to be very efficient partners in palladium-catalysed cross- coupling reactions with arenediazonium salts, affording biaryl and styrene derivatives in high yields.
Selective Coupling Reactions of Alkynyl(phenyl)iodonium Tosylates with Alkynylcopper Reagents
Kitamura, Tsugio,Tanaka, Toshimasa,Taniguchi, Hiroshi,Stang, Peter J.
, p. 2892 - 2893 (2007/10/02)
Alkynyl(phenyl)iodonium tosylates react with mixed cuprates coordinated by alkynyl components to give unsymmetrical diacetylenes selectively; the coupling reaction with dialkylcuprates afforded substituted alkynes.
