Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF-Imidoyl Sulfoxonium Ylides via Triple C-H Activation.

A condition-controlled Rh(III)-catalyzed selective synthesis of CF-substituted indoles and pyrido[2,1-]isoindoles from 2-arylpyridines and CF-imidoyl sulfoxonium ylides has been developed. The Cp*Rh(MeCN)(SbF)/HFIP system afforded CF-substituted indoles via triple C-H activation, while the [Cp*RhCl]/MeCN condition selectively furnished CF-substituted pyrido[2,1-]isoindoles through C-H [4 + 1] annulation. The notable advantages of this developed method included readily available starting materials, broad substrate scope, and excellent chemoselectivity.

Synthesis of α-Carbonyl-α'-sulfenyl Sulfoxonium Ylides in Water at Room Temperature.

An efficient synthesis of α-carbonyl-α'-sulfenyl sulfoxonium ylides through a KIO-promoted cross-dehydrogenative coupling reaction of aryl thiols and α-carbonyl sulfoxonium ylides in an aqueous medium at room temperature has been described. The α-carbonyl sulfoxonium ylides and aryl thiols adorned with various functional groups were well-tolerated and afforded moderate to high yields of α-carbonyl-α-sulfenyl sulfoxonium ylide derivatives. Finally, by converting synthesized ylide into other valuable compounds, we demonstrated the practicality of this synthetic method.

Transition-Metal-Catalyzed Directed C-H Bond Functionalization with Iodonium Ylides: A Review of the Last 5 Years.

Transition-metal-catalyzed directed C-H functionalization with various carbene precursors has been widely employed for constructing a wide range of complex and diverse active molecules through metal carbene migratory insertion processes. Among various carbene precursors, iodonium ylides serve as a novel and emerging carbene precursor with features including easy accessibility, thermal stability and high activity, which have attracted great attention from organic chemists and have achieved tremendous success in organic transformation. In this review, recent progress on the application of iodonium ylides with multifunctional coupling characteristics in C-H bond activation reactions is summarized, and the potential of iodonium ylides is discussed.

TEMPO-Mediated Dehydrogenative Hydroxyfluoroalkylation of Arylamines with Polyfluorinated Alcohols.

An efficient 2,2,6,6-tetramethylpiperidinooxy (TEMPO)-mediated hydroxyfluoroalkylation of arylamines with polyfluorinated alcohols via a radical-triggered C(sp)-H/C(sp)-H dehydrogenative cross-coupling process was developed. This transformation features simple operation, high atom economy, broad substrate compatibility, and excellent regioselectivity, leading to a series of hydroxyfluoroalkylated arylamine derivatives. Importantly, these synthetic products were further used to evaluate the antitumor activity in cancer cell lines by Cell Counting Kit-8 assay and the outcomes indicated that some compounds show a potent antiproliferative effect.

Peroxygenase-Enabled Reductive Kinetic Resolution for the Enantioenrichment of Organoperoxides.

Enantiomerically pure organoperoxides serve as valuable precursors in organic transformations. Herein, we present the first examples of unspecific peroxygenase catalyzed kinetic resolution of racemic organoperoxides through asymmetric reduction. Through meticulous investigation of the reaction conditions, it is shown that the unspecific peroxygenase from Agrocybe aegerita (AaeUPO) exhibits robust catalytic activity in the kinetic resolution reactions of the model substrate with turnover numbers up to 60000 and turnover frequency of 5.

Green synthesis and anti-tumor efficacy via inducing pyroptosis of novel 1H-benzo[e]indole-2(3H)-one spirocyclic derivatives.

Pyroptosis induction is anticipated to be a new approach to developing anti-tumor medications. A novel class of spirocyclic compounds was designed by hybridization of 1H-Benzo[e]indole-2(3H)-one with 1,4-dihydroquinoline and synthesized through a new green "one-pot" synthesis method using 10 wt% SDS/HO as a solvent to screen novel tumor cell pyroptosis inducers. The anti-tumor activity of all compounds in vitro was determined by the MTT method, and a fraction of the compounds showed good cell growth inhibitory activity.

KBrO-Promoted Cross-Dehydrogenative Coupling Reaction: An Odorless Regioselective Sulfenylation of Imidazoheterocycles in Water.

A regioselective metal-free sulfenylation of imidazoheterocycles with heterocyclic thiols or thiones has been achieved using a cross-dehydrogenative coupling method in water. In addition, the procedure has several advantages including green solvents, free of foul-smelling sulfur sources, and mild conditions, thus providing considerable application potential in the pharmaceutical industry.

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids.

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and S1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

Preparation of biodiesel oil-in-water nanoemulsions by mixed surfactants for bifenthrin formulation.

Although several approaches have been reported on the development of nanoemulsions over the last few years, studies on the formation of biodiesel nanoemulsions for bifenthrin formulation by the low-energy phase inversion composition (PIC) method are still scarce. Herein, the preparation of oil-in-water (O/W) nanoemulsions suitable for pesticide application has been achieved in biodiesel by dissolving a bifenthrin/mixture of a non-ionic surfactant (NP-6) and an anionic surfactant (ABSCa)/water system by the PIC method. The mechanism of the formation of bifenthrin nanoemulsions by dripping the water phase into the oil-surfactant phase was exemplified the pseudo-ternary phase diagram.

KIO-catalyzed cross dehydrogenative coupling reaction: sulfenylation of phenol and arylamine derivatives in water at room temperature.

A metal-free direct sulfenylation of phenol and arylamine derivatives with various heterocyclic thiols and thiones using a cross dehydrogenative coupling protocol in water at room temperature has been developed. In addition, this chemical method has several advantages including odorless sulfur sources, good functional group tolerance, green solvent, and mild conditions, making it more environmentally friendly.

6-Amino-3-methyl-4-(3-nitro-phen-yl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile.

The title compound, C(20)H(15)N(5)O(3), was synthesized by the one-pot reaction of a four-component reaction protocol in aqueous medium. The pyrano[2,3-c]pyrazole system is essentially planar, with a maximum deviation of 0.026 (2) Å.

9-(1,1-Dimethyl-3-oxobut-yl)adenine.

The title compound, C(11)H(15)N(5)O, crystallizes with two independent mol-ecules in the asymmetric unit, both of which contain essentially planar imidazole and pyrimidine rings [maximum deviations = 0.002 (2) and 0.026 (2) Å, respectively, for the first mol-ecule, and 0.