54879-93-5Relevant academic research and scientific papers
Recyclable [Ru2Cl3(p-cymene)2][PF6]/Cu(OAc)2/PEG-400/H2O system for oxidative annulation of alkynes by aniline derivatives: Green synthesis of indoles
Liao, Yang,Wei, Ting,Yan, Tao,Cai, Mingzhong
, p. 1238 - 1246 (2017/02/18)
[Ru2Cl3(p-cymene)2][PF6] in a mixture of PEG-400 and water is shown to be a highly efficient catalyst for the oxidative annulation of alkynes by N-2-pyrimidyl-substituted anilines bearing a removable directing g
Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage
Lerchen, Andreas,Vásquez-Céspedes, Suhelen,Glorius, Frank
supporting information, p. 3208 - 3211 (2016/03/12)
A redox-neutral cobalt(III)-catalyzed synthetic approach for the direct synthesis of unprotected indoles showcasing an N-N bond cleavage is reported. The herein newly introduced Boc-protected hydrazines establish a beneficial addition to the limited portfolio of oxidizing directing groups for cobalt(III) catalysis. Moreover, the developed catalytic methodology tolerates a good variety of functional groups.
Rhodium(III)-Catalyzed Redox-Neutral C-H Annulation of Arylnitrones and Alkynes for the Synthesis of Indole Derivatives
Zhou, Zhi,Liu, Guixia,Chen, Yan,Lu, Xiyan
supporting information, p. 2944 - 2950 (2015/09/28)
By using a nitrone as the oxidizing directing group, a mild, practical and efficient rhodium(III)-catalyzed C-H functionalization for the synthesis of indole derivatives has been developed. This reaction obviates the need for an external oxidant and shows good functional group tolerance. The employment of a sterically hindered Mes group on the carbon center of the nitrone is crucial to produce indoles in high yield.
Rhodium(III)-catalyzed c-h activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group
Zheng, Liyao,Hua, Ruimao
supporting information, p. 2352 - 2356 (2014/03/21)
An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for RhIII-catalyzed C-H activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and Ci￡O source, whereas its N-N bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DGauto). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DGauto strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated. Copyright
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.
Palladium-catalyzed reaction of arylamine and diarylacetylene: Solvent-controlled construction of 2,3-diarylindoles and pentaarylpyrroles
Chen, Xiaopeng,Li, Xihui,Wang, Ningning,Jin, Jisong,Lu, Ping,Wang, Yanguang
experimental part, p. 4380 - 4386 (2012/09/21)
By choosing DMF and dioxane as solvent, skeletons of indoles and pyrroles were constructed from alkynes and amines in the presence of PdCl2, respectively. These Pd-catalyzed reactions were phosphane-free with high atom efficiency and could be conducted under mild basic conditions. The proposed mechanism for the selective formation of indoles and pyrroles in different solvents is also discussed in this paper. Two different kinds of Pd-catalyzed cyclizations, leading to the construction of 2,3-diarylindole and pentaarylpyrrole from the same alkyne and aniline starting materials, were approached by choosing different solvents. The mechanisms for these solvent-controlled reactions are proposed and discussed. Copyright
Cationic ruthenium(II) catalysts for oxidative C - H/N - H bond functionalizations of anilines with removable directing group: Synthesis of indoles in water
Ackermann, Lutz,Lygin, Alexander V.
, p. 764 - 767 (2012/04/17)
Cationic ruthenium(II) complexes enabled oxidative C - H bond functionalizations with anilines bearing removable directing groups. The C - H/N - H bond cleavages occurred most efficiently in water as a sustainable solvent and provided general access to va
SUBSTITUENT INFLUENCE ON THE INDOLIZATION WITH PCl3 OF SOME o,m,p-SUBSTITUTED PHENYLHYDRAZONES
Baccolini, Graziano,Marotta, Emanuela
, p. 4615 - 4620 (2007/10/02)
The indolization of deoxybenzoin o,m,p (Me, MeO, Cl), p-NO2 and m-EtO-phenylhydrazones (1) by the above reaction has been examined.All the reactions are carried out at room temperature and high yields of the corresponding indoles (2) are obtained even whe
