This article is cited in 27 scientific papers (total in 27 papers)
A novel stereoselective and catalytic C–C coupling reaction: acetylene dimerization accompanied by addition of iodine to yield (E,E)-1,4-diiodobuta-1,3-diene in the PtIV–I––I2–MeOH system
Abstract:
A new catalytic reaction – dimerization of acetylene accompanied by addition of iodine to yield (E,E)-1,4-diiodobuta-1,3-diene at 30 °C in a methanolic solution of NaI, PtIV and I2 – has been found; a plausible reaction mechanism involves intermediate formation of a cis-divinyl derivative of platinum(IV) through two subsequent triple bond iodoplatination steps followed by reductive elimination of the final product.
Document Type:
Article
Language: English
Citation:
S. A. Mitchenko, V. P. Ananikov, I. P. Beletskaya, Yu. A. Ustynyuk, “A novel stereoselective and catalytic C–C coupling reaction: acetylene dimerization accompanied by addition of iodine to yield (E,E)-1,4-diiodobuta-1,3-diene in the PtIV–I––I2–MeOH system”, Mendeleev Commun., 7:4 (1997), 130–131
Linking options:
https://www.mathnet.ru/eng/mendc4819
https://www.mathnet.ru/eng/mendc/v7/i4/p130
This publication is cited in the following 27 articles:
S. P. Bedenko, K. I. Dement'ev, A. L. Maximov, “Modern Processes for Petrochemistry Based on Acetylene (A Review)”, Pet. Chem., 62:9 (2022), 989
William J. Lording, Thomas Fallon, Michael S. Sherburn, Michael N. Paddon-Row, “The simplest Diels–Alder reactions are not endo-selective”, Chem. Sci., 11:43 (2020), 11915
Oleg V. Khazipov, Tatyana V. Krasnyakova, Denis V. Nikitenko, Marina A. Merzlikina, Ekaterina V. Khomutova, Serge A. Mitchenko, “Successive alkylation of PtII by RI to form bis-organoplatinum(IV) derivatives as key steps for cross-electrophile coupling”, Journal of Organometallic Chemistry, 867 (2018), 333
J. Cornil, A. Guérinot, J. Cossy, “Linchpin dienes: key building-blocks in the synthesis of polyenic frameworks”, Org. Biomol. Chem., 13:14 (2015), 4129
Serge A. Mitchenko, Oleg V. Khazipov, Elena S. Mitchenko, Tatyana V. Krasnyakova, “Formation and thermodynamic stability of novel methyl–vinyl derivatives of PtIV as possible intermediates for Csp3–Csp2 cross-coupling”, Journal of Organometallic Chemistry, 752 (2014), 91
S. A. Mitchenko, O. V. Khazipov, T. V. Krasnyakova, “New stereoselective $C_{sp^2 } - C_{sp^3 }$ coupling: Catalytic iodomethylation of acetylene with methyl iodide into E-1-iodopropene”, Kinet Catal, 55:3 (2014), 304
Nikolay V. Orlov, Igor V. Chistyakov, Levon L. Khemchyan, Valentine P. Ananikov, Irina P. Beletskaya, Zoya A. Starikova, “Exclusive Selectivity in the One-Pot Formation of C–C and C–Se Bonds Involving Ni-Catalyzed Alkyne Hydroselenation: Optimization of the Synthetic Procedure and a Mechanistic Study”, J. Org. Chem., 79:24 (2014), 12111
Amanda F. Lashua, Tiffany M. Smith, Hegui Hu, Lihui Wei, Damian G. Allis, Michael B. Sponsler, Bruce S. Hudson, “Commensurate Urea Inclusion Crystals with the Guest (E,E)-1,4-Diiodo-1,3-Butadiene”, Crystal Growth & Design, 13:9 (2013), 3852
S. A. Mitchenko, O. V. Khazipov, T. V. Krasnyakova, “Platinum-catalyzed addition of iodomethane to acetylene”, Russ Chem Bull, 62:4 (2013), 984
Homogeneous Catalysis with Metal Complexes, 2012, 121
Homogeneous Catalysis with Metal Complexes, 2012, 239
Mehdi Ez-Zoubir, Jack A. Brown, Virginie Ratovelomanana-Vidal, Véronique Michelet, “Iridium-catalyzed hydroiodination of functionalized alkynes”, Journal of Organometallic Chemistry, 696:1 (2011), 433
Valentine P. Ananikov, Oleg V. Hazipov, Irina P. Beletskaya, “1,4‐Diiodo‐1,3‐dienes: Versatile Reagents in Organic Synthesis”, Chemistry — An Asian Journal, 6:2 (2011), 306
Serge A. Mitchenko, Eugene V. Khomutov, Alexander A. Shubin, Yuri M. Shul'ga, “Catalytic hydrochlorination of acetylene by gaseous HCl on the surface of mechanically pre-activated K2PtCl6 salt”, Journal of Molecular Catalysis A: Chemical, 212:1-2 (2004), 345
Ernesto Quesada, A. Ulises Acuña, Francisco Amat‐Guerri, “Synthesis of Carboxyl‐Tethered Symmetric Conjugated Polyenes as Fluorescent Transmembrane Probes of Lipid Bilayers”, Eur J Org Chem, 2003:7 (2003), 1308
Valentine P. Ananikov, Djamaladdin G. Musaev, Keiji Morokuma, “Vinyl-Vinyl Coupling on Late Transition Metals through C-C Reductive Elimination Mechanism. A Computational Study”, J. Am. Chem. Soc., 124:11 (2002), 2839
Ernesto Quesada, A. Ulises Acuña, Francisco Amat-Guerri, “New Transmembrane Polyene Bolaamphiphiles as Fluorescent Probes in Lipid Bilayers”, Angew. Chem., 113:11 (2001), 2153
Valentine P. Ananikov, Djamaladdin G. Musaev, Keiji Morokuma, “Catalytic Triple Bond Activation and Vinyl-Vinyl Reductive Coupling by Pt(IV) Complexes. A Density Functional Study”, Organometallics, 20:8 (2001), 1652
Ernesto Quesada, A. Ulises Acuña, Francisco Amat-Guerri, “New Transmembrane Polyene Bolaamphiphiles as Fluorescent Probes in Lipid Bilayers”, Angew. Chem. Int. Ed., 40:11 (2001), 2095
Sergey A. Mitchenko, Eugeniy V. Khomutov, Vitaliy V. Kovalenko, Anatoliy F. Popov, Irina P. Beletskaya, “Mechanically activated transformations in the coordination sphere of platinum complexes induced by impact grinding of solid K2PtX6 (X=Cl, Br) and K2PtCl4 salts”, Inorganica Chimica Acta, 320:1-2 (2001), 31
Contact us: