538-81-8Relevant articles and documents
A SIMPLE SYNTHESIS OF TRANS, TRANS-1,3-DIENES FROM TERMINAL ALKYNES USING CoCl2/Ph3P/NaBH4
Satyanarayana, N.,Periasamy, M.
, p. 6253 - 6256 (1986)
The cobalt hydride reagent prepared in situ in THF at -20 deg C using CoCl2/NaBH4/Ph3P in the 1:1:4 ratio hydrodimerizes terminal alkynes into the corresponding trans, trans-1,3-dienes in good yields (65 to 86percent).
THE ACTIVITY OF PALLADIUM(II) SORBED ON CARBOXYLIC CATION-EXCHANGE RESINS IN THE OXIDATIVE DIMERIZATIONS OF STYRENE
Yatsimirskii, A. K.,Erokhin, A. S.,Berezin, I. V.
, p. 33 - 38 (1980)
-
Mechanism of a Suzuki-Type Homocoupling Reaction Catalyzed by Palladium Nanocubes
Elias, Welman C.,Signori, Aline M.,Zaramello, Laize,Albuquerque, Brunno L.,De Oliveira, Daniela C.,Domingos, Josiel B.
, p. 1462 - 1469 (2017)
The trans-2-phenylvinylboronic acid homocoupling reaction catalyzed by palladium nanocubes (Pd-NCs) was investigated by kinetics, spectroscopy, and poisoning experiments. The reaction was evidenced to be sensitive to the presence of the base, which acts synergistically with the substrate molecules and assists the leaching of Pd oxide (PdOx) species to the reaction medium. This species catalyzes the homocoupling reaction through the formation of Pd-Ox-B(OH)2R pretransmetalation intermediates, via coordination with the vinylboronic acid molecules, involving an oxo-palladium-type interaction. The reaction rate was not enhanced by the saturation of the reaction medium with O2, which is due to the oxidized nature of the Pd-NC surface.
Stereoselective synthesis of (Z,E)-2-phenylselenobutadienes by palladium-catalyzed cross-coupling reaction
Cai, Ming-Zhong,Huang, Jia-Di,Peng, Chun-Yun
, p. 98 - 101 (2003)
Hydrozirconation of 1-alkynes gives ( E )-alkenylzirconium complexes 3, which are cross-coupled with (E)-α-phenylselenovinyl bromides (4) in the presence of tetrakis (triphenylphosphine) palladium catalyst to afford (Z,E )-2-phenylselenobutadienes (5) in good yields.
Bramley,Le Fevre
, p. 1820,1821 (1960)
Hydrocupration of Alkynes: a Simple Synthesis of (E,E)-1,3-Dienes
Rao, S. Achyutha,Periasamy, Mariappan
, p. 495 - 496 (1987)
Copper(I) hydride species, prepared in situ in tetrahydrofuran using NaBH4-MgBr2-Et3N-CuCl or NaH-MgBr2-CuCl reagent systems, convert terminal alkynes into (E,E)-1,3-dienes in good yields.
New aspects of diphenylbutadiene photochemistry. Regiospecific Hula-twist photoisomerization
Yang, Lan-Ying,Liu, Robert S. H.,Boarman, Kelly J.,Wendt, Natalie L.,Liu, Jin
, p. 2404 - 2405 (2005)
In EPA glass at liquid nitrogen temperature, the E,E isomer of diphenylbutadiene (DPB) was photostable, while both the Z,E and Z,Z isomers underwent selective HT isomerization at center 1 giving the stable conformer of the double-bond isomerized trans product. That HT-1 was involved rather than the OBF process was shown by results of o,o-dimethyl-DPB. Formation of unstable trans product corresponded to simultaneous configurational and conformational isomerization. The regioselectivity was found not sensitive to a substituent effect, as shown by the similar reactivity in p,p- or o,o-bistrifluoromethyl-DPB. Copyright
Design of Hemilabile N,N,N-Ligands in Copper-Catalyzed Enantioconvergent Radical Cross-Coupling of Benzyl/Propargyl Halides with Alkenylboronate Esters
Wang, Peng-Fei,Yu, Jiao,Guo, Kai-Xin,Jiang, Sheng-Peng,Chen, Ji-Jun,Gu, Qiang-Shuai,Liu, Ji-Ren,Hong, Xin,Li, Zhong-Liang,Liu, Xin-Yuan
, p. 6442 - 6452 (2022/04/19)
The enantioconvergent radical C(sp3)-C(sp2) cross-coupling of alkyl halides with alkenylboronate esters is an appealing tool in the assembly of synthetically valuable enantioenriched alkenes owing to the ready availability, low toxicity, and air/moisture stability of alkenylboronate esters. Here, we report a copper/chiral N,N,N-ligand catalytic system for the enantioconvergent cross-coupling of benzyl/propargyl halides with alkenylboronate esters (>80 examples) with good functional group tolerance. The key to the success is the rational design of hemilabile N,N,N-ligands by mounting steric hindrance at the ortho position of one coordinating quinoline ring. Thus, the newly designed ligand could not only promote the radical cross-coupling process in the tridentate form but also deliver enantiocontrol over highly reactive alkyl radicals in the bidentate form. Facile follow-up transformations highlight its potential utility in the synthesis of various enantioenriched building blocks as well as in the late-stage functionalization for drug discovery.
Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes
Watanabe, Hikaru,Nakajima, Kazuki,Ekuni, Kento,Edagawa, Ryota,Akagi, Yuta,Okuda, Yasuhiro,Wakamatsu, Kan,Orita, Akihiro
, p. 2984 - 2994 (2021/03/04)
The Sonogashira coupling of 1,3,6,8-tetrabromopyrene with 4-[(-)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i -Pr 2NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly π-expanded pyrene catalyst, and their polar oxygen functionalities enabled the easy separation of the catalyst from the products via column chromatography.
Cobalt-Catalyzed Z to e Geometrical Isomerization of 1,3-Dienes
Wang, Wei,He, Shuying,Zhong, Yuqing,Chen, Jianhui,Cai, Cheng,Luo, Yanshu,Xia, Yuanzhi
, (2022/03/27)
An efficient cobalt-catalyzed geometrical isomerization of 1,3-dienes is described. In the combination of a CoCl2 precatalyst with an amido-diphosphine-oxazoline ligand, the geometrical isomerization of E/Z mixtures of 1,3-dienes proceed in a stereoconvergent manner, affording (E) isomers in high stereoselectivity. This facile transformation features a broad substrate scope with good functional group tolerance and could be scaled up to the gram scale smoothly with a catalyst loading of 1 mol %.
