36779-17-6Relevant academic research and scientific papers
Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan-Lam and cross-dehydrogenative coupling reactions
Bian, Yunyun,Chen, Chunxia,Chen, Xin,Mo, Baichuan,Peng, Jinsong,Sun, Peng
, p. 24830 - 24839 (2020/07/14)
Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan-Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan-Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)2/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO4 and KHCO3. Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives. This journal is
Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction
Cai, Yichao,Chen, Chunxia,Chen, Xin,Liu, Yajie,Peng, Jinsong,Song, Zirui,Sun, Peng,Yang, Jiaojiao
, p. 75 - 84 (2019/12/26)
Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The i
Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones
Santi, Micol,Ould, Darren M. C.,Wenz, Jan,Soltani, Yashar,Melen, Rebecca L.,Wirth, Thomas
supporting information, p. 7861 - 7865 (2019/04/25)
A novel metal-free synthesis of 3,3-disubstituted benzofuran-2-(3H)-ones through reacting α-aryl-α-diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α-arylations of α-diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes to afford valuable 3,3-disubstituted benzofuranones in good yields.
Synthesis of Substituted Indole-3-carboxylates by Iron(II)-Catalyzed Domino Isomerization of 3-Alkyl/aryl-4-aryl-5-methoxyisoxazoles
Bodunov, Vladimir A.,Galenko, Ekaterina E.,Galenko, Alexey V.,Novikov, Mikhail S.,Khlebnikov, Alexander F.
, p. 2784 - 2798 (2018/06/08)
The iron(II)-catalyzed domino isomerization of 3-alkyl/aryl-4-arylisoxazoles provides a selective access to a wide range of structurally diverse highly substituted indole-3-carboxylates. The operational simplicity, high atom efficiency, and the use of stable starting materials and an inexpensive and low-toxicity catalyst are some of the attractive features of this tandem double ring-opening-ring-closure strategy.
Copper-Catalyzed Synthesis of Multisubstituted Indoles through Tandem Ullmann-Type C-N Formation and Cross-dehydrogenative Coupling Reactions
Li, Yue,Peng, Jinsong,Chen, Xin,Mo, Baichuan,Li, Xue,Sun, Peng,Chen, Chunxia
, p. 5288 - 5294 (2018/05/17)
Multisubstituted indoles were synthesized via a one-pot tandem copper-catalyzed Ullmann-type C-N bond formation/intramolecular cross-dehydrogenative coupling process at 130 °C in DMSO. The methodology allows practical and modular assembly of indoles in go
Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds
Guo, Xin,Han, Jianwei,Liu, Yafeng,Qin, Mingda,Zhang, Xueguo,Chen, Baohua
, p. 11505 - 11511 (2017/11/10)
A rhodium-catalyzed intermolecular coupling between arylnitrones and diazo compounds by C-H activation/[4 + 1] annulation with a C(N2)-C(acyl) bond cleavage is reported, and 2,3-disubstituted NH indoles are directly synthesized in up to a 94% yield. A variety of functional groups are applicable to this reaction to give the corresponding products with high selectivity. Compared to other previously reported Rh(III)-catalyzed synthesis of homologous series, this method is simpler, more general, and more efficient.
Visible-Light-Induced Direct Photocatalytic Carboxylation of Indoles with CBr4/MeOH
Yang, Qing-Qing,Marchini, Marianna,Xiao, Wen-Jing,Ceroni, Paola,Bandini, Marco
supporting information, p. 18052 - 18056 (2015/12/24)
Photocatalysis enables the cascade reactions of indoles and CBr4 in MeOH through a C(sp2)-H functionalization/methanolysis sequence. The title reaction provides an efficient access to indole 2- and 3-carboxylates in a single operation (no preinstallation of protecting as well as directing groups was required) with good yields under mild reaction conditions. Shedding light on indole: The regioselective alkoxycarboxylation of indoles and heteroarenes using the CBr4/MeOH couple was accomplished through visible-light-induced photoredox catalysis. The described photocatalytic strategy features operational simplicity as well as high functional-group tolerance and represents a direct procedure to access indole carboxylates in generally moderate to good yields (see scheme).
Efficient synthesis of useful heterocycles via transition metal-catalyzed cascade processes
Tanimori, Shinji,Inaba, Ushio,Kato, Yoshihiro,Ura, Haruna,Kashiwagi, Hiroaki,Nishimura, Takeshi,Kirihata, Mitsunori
, p. 2157 - 2164 (2014/06/24)
This paper reports our recent results from synthesis of some useful heterocycles, for example oxazolidinones, indoles, and quinoxalinones, by transition metal-catalyzed cascade processes. The scope and limitations of these procedures and the reaction mech
Regioselective synthesis of indoles via rhodium-catalyzed C-H activation directed by an in-situ generated redox-neutral group
Muralirajan, Krishnamoorthy,Cheng, Chien-Hong
supporting information, p. 1571 - 1576 (2014/06/09)
A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in-situ generated oxidizing directing group -N-Ni'CR1R2 assisted ortho-C-H activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom-step economical.
