847237-13-2Relevant academic research and scientific papers
Pd-catalyzed C–H bond activation of Indoles for Suzuki reaction
Banerjee, Isita,Ghosh, Keshab Ch,Sinha, Surajit
, (2019/08/22)
Abstract: We present a practical method for Suzuki coupling by which unprotected or N-protected indoles may be selectively arylated in the C2-position through direct C–H bond activation by electrophilic Pd(TFA) 2 catalyst. The protocol is operationally simple as it is carried out in dioxane/water mixture, and air as the sole oxidant at room temperature. Various 2-arylated indoles were obtained in good yields. The protocol works for benzofuran, pyrrole and thiophene also. Graphic abstract: Selective C-2 arylation of heterocycles using Pd(II) catalyst via C–H activation was performed under ambient condition. C3–C2 migration of organopalladium intermediate controls the reaction pathway.[Figure not available: see fulltext.].
Iridium(I)-Catalyzed C?H Borylation in Air by Using Mechanochemistry
Pang, Yadong,Ishiyama, Tatsuo,Kubota, Koji,Ito, Hajime
supporting information, p. 4654 - 4659 (2019/03/17)
Mechanochemistry has been applied for the first time to an iridium(I)-catalyzed C?H borylation reaction. By using either none or just a catalytic amount of a liquid, the mechanochemical C?H borylation of a series of heteroaromatic compounds proceeded in air to afford the corresponding arylboronates in good-to-excellent yields. A one-pot mechanochemical C?H borylation/Suzuki–Miyaura cross-coupling sequence for the direct synthesis of 2-aryl indole derivatives is also described. The present study constitutes an important milestone towards the development of industrially attractive solvent-free C?H bond functionalization processes in air.
A Three-Component Strategy for Benzoselenophene Synthesis under Metal-Free Conditions Using Selenium Powder
Ni, Penghui,Tan, Jing,Zhao, Wenqi,Huang, Huawen,Xiao, Fuhong,Deng, Guo-Jun
supporting information, p. 3518 - 3522 (2019/05/24)
An efficient three-component benzoselenophenes formation has been developed from substituted indoles, acetophenones, and selenium powder under metal-free conditions. 2-Aryl indoles played an important role to promote benzoselenophene formation from acetophenone derivatives and selenium powder. One C-C and two C-Se bonds were selectively formed to provide 40 new benzoselenophenes in good yields.
Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
Fortes, Margiani P.,Da Silva, Paulo B.N.,Da Silva, Teresinha G.,Kaufman, Teodoro S.,Milit?o, Gardenia C.G.,Silveira, Claudio C.
, p. 21 - 26 (2016/05/10)
A novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.
Electrochemical-mediated cyclization of 2-alkynylanilines: A clean and safe synthesis of indole derivatives
Arcadi, Antonio,Bianchi, Gabriele,Inesi, Achille,Marinelli, Fabio,Rossi, Leucio
experimental part, p. 783 - 787 (2009/04/11)
The electrochemical-mediated annulation of 2-alkynylanilines to the corresponding indole derivatives proceeds in good yields and under conditions that avoid the use of metal catalysts or classical organic acids and bases. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
