76836-54-9Relevant academic research and scientific papers
Controllable construction of isoquinolinedione and isocoumarin scaffolds: Via RhIII-catalyzed C-H annulation of N -tosylbenzamides with diazo compounds
Liu, Yanfei,Wu, Jiaping,Qian, Baiyang,Shang, Yongjia
, p. 8768 - 8777 (2019/10/16)
A highly efficient protocol for the synthesis of isoquinolinediones by RhIII-catalyzed C-H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C-H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.
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 (2018/05/08)
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
Method of synthesizing heterocyclic compound by light-induced non-metal catalyzed carbon aryl serial reactions
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Paragraph 0030, (2019/01/08)
The invention belongs to the technical field of organic synthesis and discloses a method of synthesizing a heterocyclic compound by light-induced non-metal catalyzed carbon aryl serial reactions. Themethod comprises the following steps: stirring substrate
Rhodium(I)-Catalyzed Decarbonylative Aerobic Oxidation of Cyclic α-Diketones: A Regioselective Single Carbon Extrusion Strategy
Golime, Gangadhararao,Kim, Hun Young,Oh, Kyungsoo
, p. 942 - 945 (2018/02/22)
A rhodium-catalyzed decarbonylative aerobic oxidation of cyclic α-diketones has been developed for the first time, where the regioselective formations of α-pyrones and isocoumarins have been achieved. The current decarbonylative aerobic oxidation pathway proceeds via the C-C bond cleavage followed by a C-O bond formation, representing a biomimetic oxidation approach to unsaturated six-membered cyclic lactones. The unique ability of rhodium catalysts to induce the decarbonylative aerobic oxidation opens up a new synthetic toolbox that utilizes the "regioselective single carbon" extrusion strategy.
Oxidative Annulation of Arenecarboxylic and Acrylic Acids with Alkynes under Ambient Conditions Catalyzed by an Electron-Deficient Rhodium(III) Complex
Kudo, Eiji,Shibata, Yu,Yamazaki, Mutsumi,Masutomi, Koji,Miyauchi, Yuta,Fukui, Miho,Sugiyama, Haruki,Uekusa, Hidehiro,Satoh, Tetsuya,Miura, Masahiro,Tanaka, Ken
supporting information, p. 14190 - 14194 (2016/09/23)
It has been established that an electron-deficient CpErhodium(III) complex catalyzes the oxidative [4+2] annulation of substituted arenecarboxylic and acrylic acids with alkynes under ambient conditions (at RT–40 °C, under air) without using excess amounts of substrates to produce the corresponding substituted isocoumarins and α-pyrones in high yields. Minor modification of reaction conditions depending on the coordination ability of alkynes realized the high efficiency.
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 (2013/10/22)
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.
Synthesis of (1H)-isochromen-1-imines by nickel-catalyzed reaction of 2-iodobenzamides with alkynes
Miura, Tomoya,Hiraga, Kentaro,Toyoshima, Takeharu,Yamauchi, Motoshi,Murakami, Masahiro
, p. 798 - 800 (2012/09/07)
2-Iodobenzamides reacted with alkynes in the presence of a nickel(0)/P(4-ClC6H4)3 catalyst to produce substituted (1H)-isochromen-1-imines. The reaction proceeded through the formation of an oxanickelacycle, alkyne insertion, and reductive elimination.
Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage
Ueura, Kenji,Satoh, Tetsuya,Miura, Masahiro
, p. 5362 - 5367 (2008/02/08)
(Chemical Equation Presented) The oxidative coupling of benzoic acids with internal alkynes effectively proceeds in the presence of [Cp*RhCl 2]2 and Cu(OAc)2·H2O as catalyst and oxidant, respectively, to produce
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 (2007/10/03)
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
CONVERSION ANODIQUE D'INDENONES EN MILIEU NUCLEOPHILE : UNE SYNTHESE FACILE DE 4-ARYL ISOCOUMARINES PAR TRANSPOSITION DES PRODUITS D'OXYDATION
Delaunay, Jacques,Simonet, Jacques
, p. 543 - 544 (2007/10/02)
Substituted indenones may be easily converted into 4-aryl isocoumarines when oxidized anodically in some nucleophilic solvents.For that, the electrolysis solution has to be added to a strong acid before the work up.
