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
Cyclooctadiene iridium complexes [Cp*Ir(COD)X]+ (X = Cl, Br, I): Synthesis and application for oxidative coupling of benzoic acid with alkynes
Datsenko, Vera P.,Nelyubina, Yulia V.,Smol'yakov, Alexander F.,Loginov, Dmitry A.
, p. 7 - 12 (2018)
The cyclooctadiene iridium complexes [Cp*Ir(COD)X]PF6 ([1a?c]PF6; X = Cl, Br, I) were synthesized by reactions of Cp*Ir(COD) with halogens followed by a counterion exchange. The cyclooctadiene in these complexes is a thermally labile
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.
Rhodium(III)-Catalyzed C(sp2)-H Chemoselective Annulation to O-Cyclized Isochromen-imines from Benzamides
Zhang, Ping,Chang, Wenju,Kang, Yan-Shang,Zhao, Wenxuan,Cui, Pei-Pei,Liang, Yong,Sun, Wei-Yin,Lu, Yi
, p. 9462 - 9467 (2020)
Through the development of ligands and reaction conditions, the Rh(III)-catalyzed selective annulation of benzamides with internal alkynes has been achieved to the formation of O-cyclized isochromen-imines. Various substituents are well-tolerated under mild reaction conditions. Density functional theory calculations indicate that silver carbonate could act as a Lewis acid to assist the ligand to improve the chemical selectivity of the reaction in a catalytic system.
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
Cross-Dehydrogenative N-N Coupling of Aromatic and Aliphatic Methoxyamides with Benzotriazoles
Vemuri, Pooja Y.,Patureau, Frederic W.
, p. 3902 - 3907 (2021)
Nitrogen-nitrogen bond containing motifs are ubiquitous in bioactive compounds and organic materials. However, intermolecular hetero-selective N-H/N-H oxidative coupling reactions remain very challenging and largely unexplored. Here, we report an unprecedented, simple and hetero-selective cross-dehydrogenative N-N coupling of amides and benzotriazoles, utilizing only a hypervalent iodine species as the terminal oxidant. The scope and mechanistic investigations are discussed.
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
An efficient waste-free oxidative coupling via regioselective C-H bond cleavage: Rh/Cu-catalyzed reaction of benzoic acids with alkynes and acrylates under air
Ueura, Kenji,Satoh, Tetsuya,Miura, Masahiro
, p. 1407 - 1409 (2007)
Figure presented The direct oxidative coupling of benzoic acids with internal alkynes proceeds efficiently in the presence of a rhodium/copper catalyst system under air to afford the corresponding isocoumarin derivatives. The reaction forms no wastes exce
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
μ-Borole triple-decker complexes as catalysts for oxidative coupling of benzoic acid with alkynes. Structure of a hybrid rhodacyclopentadienyl/borole triple-decker complex
Loginov, Dmitry A.,Muratov, Dmitry V.,Nelyubina, Yulia V.,Laskova, Julia,Kudinov, Alexander R.
, p. 393 - 397 (2017)
Reaction of dimethylamine adduct of 1-methyl-3-borolene with [(C2H4)2RhCl]2 gives the triple-decker complex (η-C4H4BMe)Rh(μ-η:η-C4H4BMe)Rh(η-C4H4
