1684-07-7Relevant articles and documents
Effect of Cp-Ligand Methylation on Rhodium(III)-Catalyzed Annulations of Aromatic Carboxylic Acids with Alkynes: Synthesis of Isocoumarins and PAHs for Organic Light-Emitting Devices
Molotkov, Alexander P.,Arsenov, Mikhail A.,Kapustin, Daniil A.,Muratov, Dmitry V.,Shepel', Nikolay E.,Fedorov, Yury V.,Smol'yakov, Alexander F.,Knyazeva, Elena I.,Lypenko, Dmitry A.,Dmitriev, Artem V.,Aleksandrov, Alexey E.,Maltsev, Eugeny I.,Loginov, Dmitry A.
, p. 334 - 345 (2020)
An efficient protocol was developed for the synthesis of π-extended isocoumarins and polycyclic aromatic hydrocarbons based on the oxidative coupling of aromatic carboxylic acids with internal alkynes catalyzed by (cyclopentadienyl)rhodium complexes. The
Cp*IrIII-catalyzed oxidative coupling of benzoic acids with alkynes
Frasco, Daniel A.,Lilly, Cassandra P.,Boyle, Paul D.,Ison, Elon A.
, p. 2421 - 2429 (2013)
Cp*Ir(III) complexes have been shown to catalyze the oxidative coupling of benzoic acids with alkynes in methanol at 60 C to form a variety of isocoumarins. The use of AgOAc as an oxidant was required to facilitate significant product formation. Alkyl alkynes were shown to be more reactive substrates than aryl alkynes, and a number of functional groups were tolerated on benzoic acid. Combined mechanistic and computational studies (BP86) revealed that (1) C-H activation occurs via an acetate-assisted mechanism; (2) C-H activation is not turnover limiting; and (3) the oxidant oxidizes the reduced form of the catalyst via an Ir(I)-Ir(II)-Ir(III) sequence.
Cationic iridacarboranes [3-(arene)-3,1,2-IrC2B9H11]+ and [3-(MeCN)3-3,1,2-IrC2B9H11]+: Synthesis, reactivity, and bonding. Catalysis of oxidative coupling
Loginov, Dmitry A.,Belova, Alena O.,Vologzhanina, Anna V.,Kudinov, Alexander R.
, p. 232 - 240 (2015)
(Arene)iridacarboranes [3-(arene)-3,1,2-IrC2B9H11]+ (arene = benzene (1a), toluene (1b), o-xylene (1c), m-xylene (1d), durene (1e)) were synthesized by reaction of [(cod)IrCl]2 with Tl[Tl(η-7,8-C
Computational Characterization of the Mechanism for the Oxidative Coupling of Benzoic Acid and Alkynes by Rhodium/Copper and Rhodium/Silver Systems
Funes-Ardoiz, Ignacio,Maseras, Feliu
, p. 12383 - 12388 (2018)
DFT calculations were applied to study the oxidative coupling between benzoic acid and 1-phenyl-1-propyne catalyzed by [CpRhCl2]2 (Cp=cyclopentadienyl) by using either Cu(OAc)2(H2O) or Ag(OAc) as the terminal ox
Rhodacarboranes as catalysts for oxidative coupling of benzoic acid with diphenylacetylene
Loginov,Belova,Kudinov
, p. 983 - 986 (2014)
Rhodacarboranes [(9-SMe2-7,8-Me2-C2B9H8)RhCl2]2, [(1-ButNH-1,7,9-C3B8H10)-RhI2]2, [(9-SMe2-7,8-C
Synthesis of Benzo-Fused Cyclic Compounds via Rhodium-Catalyzed Decarboxylative Coupling of Aromatic Carboxylic Acids with Alkynes
Inai, Yasuhito,Usuki, Yoshinosuke,Satoh, Tetsuya
supporting information, p. 3029 - 3036 (2021/04/15)
The decarboxylative coupling of diversely substituted benzoic acids with internal alkynes proceeds smoothly in the presence of a [RhCl(cod)] 2/1,2,3,4-tetraphenyl-1,3-cyclopentadiene catalyst system to selectively produce highly substituted nap
Selective annulation of benzamides with internal alkynes catalyzed by an electron-deficient rhodium catalyst
Zhang, Ping,Chang, Wenju,Jiao, Hongyun,Kang, Yanshang,Zhao, Wenxuan,Cui, Peipei,Liang, Yong,Sun, Wei-Yin,Lu, Yi
supporting information, p. 1717 - 1720 (2021/03/03)
An electron-deficient [CpERhCl2]2 catalyzed annulation of N-pentafluorophenylbenzamides with internal alkynes was successfully established under mild reaction conditions, with the assistance of Lewis acid silver salt. Particularly, electron-deficient benzamide substrates were smoothly transformed into the desired products in this catalytic system. The catalytic system showed a broad tolerance for different substituents on the aromatic rings or aryl, alkyl-substituted alkynes.
