A method for combinative oxidative homo dimerization and cyanomethylation of free indole derivatives catalysed by TEMPO and Pd(OAc)2 was demonstrated for the first time. This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable 2-(2-(1H-indol-3-yl)-3-oxoindolin-2-yl)acetonitriles in moderate to excellent yields.

A combinative C2-selective arylation, and C3-selective carbonylation of free indole derivatives, by means of TEMPO catalysis and a silver oxidant under non-directing group conditions, was successful demonstrated. This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable 3,2′-biindolin-2-ones in moderate to excellent yields.

A combinative C2-selective arylation, and C3-selective carbonylation of free indole derivatives, by means of TEMPO catalysis and a silver oxidant under non-directing group conditions, was successful demonstrated. This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable 3,2′-biindolin-2-ones in moderate to excellent yields.

Mild conditions have been developed to achieve NBS-induced homodimerization of indole derivatives with excellent regioselectivity at 15 °C in high efficiency. This method provides a simple route to a 2,3′-linked biindolyl scaffold from the electron-rich to moderately electron-poor indoles. In addition, [3,2-a]carbazole derivatives can also be prepared through this method.

•Monometallic Rh and Ni nanoparticles can spontaneously alloy into bimetallic RhNi nanoparticles.•RhNi alloy nanoparticles have been characterized by XRD, SAED, HAADF-STEM, and EDS.•RhNi alloy nanocatalysts exhibit much higher performance in the catalytic dehydrogenation of hydrous hydrazine.Chemical hydrogen storage, endowed with superiorities of safety and efficiency, has been regarded as one of the most promising approaches. The design and synthesis of metallic catalytic system is an key step for development of chemical hydrogen storate materials. In this paper, we report that RhNi nanocatalyst, formed by spontaneously alloying of well-dispersed Rh and Ni NPs, exhibits much higher performance in the catalytic dehydrogenation of hydrous hydrazine.RhNi nanocatalyst, formed by spontaneously alloying of well-dispersed Rh and Ni NPs, exhibits much higher performance in the catalytic dehydrogenation of hydrous hydrazine.

•The Pd-catalyzed oxidative homocoupling of two N-oxide C–H bonds.•It is highly regioselective (5,5′-linkage).•The reaction showed good compatibility with halogen-containing substituent.A convenient and highly regioselective palladium-catalyzed direct C–H homocoupling of 1,2,3-triazole N-oxides was developed in the presence of silver carbonate and 1,10-phenanthroline. This protocol provides a straightforward and operationally simple route for the preparation of bis(1,2,3-triazole)3,3′-dioxides in good to excellent yields.

An efficient nickel-catalyzed protocol for C–S cross-coupling through the direct functionalization of 2-aryl-1,2,3-triazole N-oxide C–H bonds with aryl or alkyl thiols, or diphenyl disulfide has been developed. The targeted N+–O− bond cleavage can be observed during the reaction, and thus obviates the need to use an additional deoxygenation step. This new protocol for the preparation of thiolated 2-aryl-1,2,3-triazoles appears to offer good yields with high regioselectivity, mild conditions, and a wide substrate scope.

•A novel series of bisindole derivatives bearing oxime moiety were synthesized.•Some of compounds showed good anti-proliferative activities against tumor cells than the commercial anticancer drug 5-Fu.•Representative compounds 4e may induce apoptosis through a mitochondrion-dependent pathway.•4e effectively arrested T24 cells in G1 stage and possibly has an effect on cell cycle regulatory proteins.In an effort to develop potent anti-cancer chemopreventive agents, a novel series of bisindole derivatives bearing oxime moiety were synthesized. Structures of all compounds were characterized by NMR and HRMS. Anti-proliferative activities for all of these compounds were investigated by the method of MTT assay on 7 human cancer lines and the normal cell lines (HUVEC). Most of them showed a noteworthy anti-cancer activity in vitro, the half maximal inhibitory concentration (IC50) value is 4.31 μM of 4e against T24. The results from Hoechst 33258 and acridine orange/propidium iodide staining as well as annexinV-FITC assays provided evidence for an apoptotic cell death. The further mechanisms of compound 4e-induced apoptosis in T24 cells demonstrated that compound 4e induced the productions of ROS, and altered anti- and pro-apoptotic proteins, leading to mitochondrial dysfunction and activations of caspase-9 and caspase-3 for causing cell apoptosis. Moreover, the cell cycle analysis and western-blot analysis indicated that compound 4e effectively arrested T24 cells in G1 stage and possibly has an effect on cell cycle regulatory proteins particularly cyclin D1.A series of bisindole derivatives bearing oxime moiety were synthesized. Representative compound 4e may induce apoptosis through a mitochondrion-dependent pathway and possibly has an effect on cell cycle regulatory proteins.

An oxidative homo dimerization of free indole derivatives, by means of silver catalysis and TEMPO oxidant, was first successful demonstrated. This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable substituted C3–C3′ bisindolin-2-ones in moderate to excellent yields.

A highly stereoselective and efficient transition-metal-free semihydrogenation of internal alkynes to E-alkenes using cheap and green water as hydrogen donor is described. The reactions are conducted under convenient conditions and provide products in good to excellent yields, with broad substrate scope, including a variety of diarylalkynes.

A general and efficient method for the cross-coupling of indoles with β-keto esters by using TEMPO/CuSO4·5H2O in air as oxidant has been developed. This reaction features high functional-group compatibility and an excellent selectivity. This methodology provides an alternative approach for the ketonization–olefination of indoles in moderate to good yields.

An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid was achieved from (S)-glutamic acid via the furylation of an N-protected 6-hydroxy-2-piperidinone using furan as a nucleophile and the oxidation of the furyl group to a carboxylic group as the key steps.(5S,6R)-1-Benzyl-5-benzyloxy-6-hydroxy-2-piperidinoneC19H21NO3[α]D25=-29.8(c1.0,CHCl3)Source of chirality: (S)-glutamic acidAbsolute configuration: (5S,6R)(5S,6S)-1-Benzyl-5-benzyloxy-6-(2-furyl)-2-piperidinoneC23H23NO3[α]D25=-54.9(c0.8,CHCl3)Source of chirality: (S)-glutamic acidAbsolute configuration: (5S,6S)(5S,6S)-1-Benzyl-5-benzyloxy-2-piperidinone-6-carboxylic acidC20H21NO4[α]D25=-109.9(c1.0,CHCl3)Source of chirality: (S)-glutamic acidAbsolute configuration: (5S,6S)(5S,6S)-1-Benzyl-5-benzyloxy-2-piperidinone-6-carboxylic acid methyl esterC21H23NO4[α]D20=-52.9(c2.1,CHCl3)Source of chirality: (S)-glutamic acidAbsolute configuration: (5S,6S)(2S,3S)-1-Benzyl-3-benzyloxypiperidine-2-carboxylic acid methyl esterC21H25NO3[α]D25=-19.0(c1.5,CHCl3)Source of chirality: (S)-glutamic acidAbsolute configuration: (2S,3S)(2S,3S)-3-Hydroxypipecolic acidC6H11NO3[α]D25=+13.3(c0.7,10%aq HCl)Source of chirality: (S)-glutamic acidAbsolute configuration: (2S,3S)

A method for the combinative oxidative homo dimerization and cyanation of free indole derivatives catalysed by TEMPO along with silver carbonate was demonstrated for the first time This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable 2-(1H-indol-3-yl)-3-oxoindoline- 2-carbonitriles in moderate to excellent yields. Furthermore, selected compounds 6b and 6g exhibit moderate to good anti-schistosomicidal activities.

A method for combinative oxidative homo dimerization and cyanomethylation of free indole derivatives catalysed by TEMPO and Pd(OAc)2 was demonstrated for the first time. This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable 2-(2-(1H-indol-3-yl)-3-oxoindolin-2-yl)acetonitriles in moderate to excellent yields.

A general and efficient method for the cross-coupling of indoles with β-keto esters by using TEMPO/CuSO4·5H2O in air as oxidant has been developed. This reaction features high functional-group compatibility and an excellent selectivity. This methodology provides an alternative approach for the ketonization–olefination of indoles in moderate to good yields.

An efficient nickel-catalyzed protocol for C–S cross-coupling through the direct functionalization of 2-aryl-1,2,3-triazole N-oxide C–H bonds with aryl or alkyl thiols, or diphenyl disulfide has been developed. The targeted N+–O− bond cleavage can be observed during the reaction, and thus obviates the need to use an additional deoxygenation step. This new protocol for the preparation of thiolated 2-aryl-1,2,3-triazoles appears to offer good yields with high regioselectivity, mild conditions, and a wide substrate scope.