Substituted pyrroles are prevalent aromatic ring systems encountered in numerous natural products and bioactive molecules. Herein, a novel ynamide scaffold has been designed, synthesized and subsequently applied to an unprecedented gold-catalyzed and PTSA-assisted cascade cycloisomerization reaction for the synthesis of b-pyrrole substituted a, b-unsaturated ketones. Notably, the reaction is stereoselective

Herein, we report a metal-free approach to construct C-X (X=S, Se) bonds with the broadly available N-hydroxyphthalimide esters and disulfides/diselenides (Ar2X2,X = S or Se) using bis(pinacolato)diboron as the reductant. Density functional theory calculations and control experiments reveal that such a C-X bond formation process is reductive decarboxylationmediated from pyridine-boryl radical to yield

An electrochemical oxidative three-component tandem reaction of arylhydrazines, 1,3-diketones and ammonium thiocyanate has been established to construct 4-thiocyanato-1H-pyrazoles under metal-, oxidant-free and mild conditions in an undivided cell. Various 4-thiocyanato-1H-pyrazole derivatives could be obtained with broad substrate scope, excellent functional group tolerance from available raw materials

In recent years, continuous flow technology have been applied to C−H activation to improve reaction efficiency. Herein, various imines and alkynes have been smoothly applied to continuous flow system. A series of spirocyclic sultams and isoquinolines can be obtained in excellent yields via [3+2] or [4+2] annulation reactions under relatively mild conditions.

Kinetic models are widely used in simulating the relationship between the input space and the outcome space of a chemical process. Ignoring the computational cost, complete profiling, i.e., performing simulations at all grid points in the input space, would be the best way to understand the model because it provides us with a complete picture of intervariable relationships. Optimization methods that

An efficient and straightforward approach for the synthesis of trifluoromethyl-decorated benzo[de][1,8]naphthyridines has been achieved via the Rh(III)-catalyzed dual C–H activation and cascade annulation of benzimidates and CF3-imidoyl sulfoxonium ylides. The novel transformation involves the formation of four new chemical bonds along with the release of two molecules of dimethyl sulfoxide (DMSO)

Catalytic asymmetric hydrosilylation is an extremely important and atom-economical chemical transformation in the field of catalysis and synthetic chemistry. Although stereospecific hydrosilylation provides a general strategy for elaborating diastereo- and enantioselective synthesis of optically pure organosilicon compounds, existing methods for accessing Si-C bond-forming hydrosilylation of alkenes

Herein, we report a new method for the synthesis of aminodiborane (µ-NH2B2H5), by the reaction of NH3BH3 and elemental iodine (I2). The in situ generated aminodiborane is used as a reagent for the reduction of carboxamides to amines. This method is applicable to various secondary amides, tertiary amides, and trifluoroamides with yields obtained in the range of 67-94%. This protocol is also useful for

The construction of tunable multi-smart luminescent materials induced by noncovalent supramolecular interactions has become one of the most important topics in luminescent materials research. Herein, we reported novel tunable multi-color luminescent supramolecular assemblies based on cucurbit[10]uril (CB[10])-enhanced noncovalent heterodimers intermolecular charge-transfer interactions. Through host-enhanced

Based on the goals of sustainability and environmentally conscious science, great progress has been made in the field of green chemical synthesis, but a synthesis that combines high levels of step economy with high levels of efficiency and scalability has remained elusive. In this research, highly efficient and scalable total synthesis of potent anti-inflammatory pesimquinolone I (1) with a unique

6-Alkyl-6-hydroxycyclohexa-2,4-dienone derivatives, commonly referred to as ortho-quinols, and their simple ester and ether variants constitute a class of organic compounds that aroused much interest amongst chemists over the past 70 years for several reasons related to organic synthesis, natural product chemistry and biochemistry. It was very early on that organic chemists understood the potential

α-Hydroxy amides are an essential class of compounds found in natural products and bioactive molecules of drug candidates. Herein we report a facile and direct approach to these compounds through oxalic acid decarbonylation/decarboxylation during the Passerini three-component reaction (P-3CR) under solvent-free conditions, with microwave heating. This very convenient methodology provides the title

We report herein the application of 1,1-bis[(pinacolato)boryl]methane as a new type of terminating reagents to realize three-component coupling reaction with aryl iodide and different electrophiles. A series of ortho-disubstituted benzylboronates can be synthesized and the ortho-substituent can be varied by using bromoacetic esters or O-benzoyl hydroxylamine as electrophiles with slightly modified

Fused tricyclic hydronaphthofurans with multiple chiral centers are very important skeletons for constructing natural products; however, their synthesis is challenging, and a detailed understanding of the final formation mechanism remains elusive. In this work, density functional theory computations were employed to characterize rhodium-catalyzed [2+2+2] cycloaddition of enyne with terminal alkynes

A carboxylate-assisted iridium(III)-catalyzed regioselective C(sp2)–H heteroarylation/esterification reaction of acrylic acid is disclosed herein for the first time. This catalytic protocol tolerates various α-substituted, β-substituted, and α, β-disubstituted acrylic acids as well as heteroaromatic boronates well. The resulting 3,4-dihydro-2H-pyran-6-carboxylic acid derivative 3r highlighted the AIE-active

We report a general, catalyst-controlled route to prostaglandin F2α and its analogues. The approach uses a Rh-catalyzed dynamic kinetic asymmetric Suzuki–Miyaura coupling reaction between a racemic bicyclic allyl chloride and alkenyl boronic esters bearing chiral alcohols to give cyclopentyl intermediates bearing 3 contiguous stereocenters. The route provides advanced intermediates in 99% ee as a single

In this paper, a thermally-induced intramolecular [2 + 2] cycloaddition of allenene-methylenecyclopropanes has been excavated for the rapid construction of nitrogen containing heterocycles spiro[bicyclo[3.2.0]heptane-6,1'-cyclopropane] and spiroheptane-2,1'-cyclopropane cyclic frameworks in excellent total yields with good functional group compatibility under relatively mild conditions. These two heterocycles

We report herein a concise and useful method to the construction of 3 substituted indole derivatives via palladium catalyzed ring-opening coupling reaction of cyclopropanols with N-allenyl-2-iodoanilines. Various indoles bearing different function group have been synthesized in moderate to good yield. Furthermore, gram-scale experiment and diverse transformation of the products showed a great potential

Notwithstanding recent developments in nickel-catalyzed C-O cross-coupling chemistry, such transformations of substituted phenols and (hetero)aryl chlorides with a useful reaction scope have yet to be reported. In this work, we disclose the results of catalyst screening that allowed the identification of PhPAd-DalPhos/NiCOD2 as an effective catalyst system under thermal conditions for the O-arylation

Diarylselenides are a representative class of molecules in organoselenium compounds. We herein report a Rh-catalyzed direct diarylation of selenium with benzamide derivatives. The use of elemental selenium as the Se source is intriguing in terms of atom economy, cost, stability, and handling. A series of diarylselenides with amide moieties were readily accessible through directed C-H activation. The

General routes for the synthesis of silica-immobilized symmetrical and unsymmetrical salophen and salen ligands and metal complexes have been developed starting from the natural product 4-allylanisole (methyl-chavicol and estragole). The key step of the syntheses is a microwave-assisted, platinum oxide catalyzed hydrosilylation of the terminal alkene of 5-allyl-2-hydroxybenzaldehyde to afford a sol-gel

The participation of the tether moiety in fullerene recognition of corannulene-based molecular tweezers is known to be an important factor. In the present work, we describe the synthesis of a set of fullerene receptors bearing two corannulene units located at a suitable distance to effectively interact with C60 and C70. The tether comprises a fluorene-like scaffold where an assortment of different

A straightforward protocol for the synthesis of 11-trifluoromethylated dibenzodiazepines has been developed via TBAC-induced trifluoromethylation/cyclization of o-isocyanodiaryl amines using Togni's reagent as the trifluoromethyl source. This is the first report on the one-step construction of CF3-containing dibenzodiazepine drug skeletons. Additionally, a series of 11-trifluoromethylated dibenzodiazepines

A one-pot, metal-free, light-driven [4+2]-cycloaddition reaction is described by accessing a diverse collection of chromeno[4,3-b]quinoline and chromeno[4,3-b][1,8]naphthyridine scaffolds in a diastereoselective manner. This process delivered stereoisomers, which were challenging to produce by an inverse-demand Diels-Alder reaction. The tetracyclic products were provided in good yields, promoted by

Glycerophospholipids are major components of cellular membranes and provide important signaling molecules. Besides shaping membrane properties, some bind to specific receptors to activate biological pathways. Untangling the roles of individual glycerophospholipids requires clearly defined molecular species, a challenge that can be best addressed through chemical synthesis. However, glycerophospholipid

Ceramides (Cer) are bioactive sphingolipids that have been proposed as potential disease biomarkers since they are involved in several cellular stress responses, including apoptosis and senescence. 1-Deoxyceramides (1-deoxyCer), a particular subtype of noncanonical sphingolipids, have been linked to the pathogenesis of type II diabetes. To investigate the metabolism of these bioactive lipids, as well

The effect of counter-anion on enantio-control in oxidative NHC catalysis was demonstrated systematically for the first time. For kinetic resolution of oxindole-derived tertiary alcohols through NHC-catalyzed esterification, the identity of anions, either in the form of an additive or as the counter-anion in the azolium pre-catalyst, showed a significant effect on the enantioselectivity of the catalytic

Direct C-H amination methods are essential because of the importance of aryl amine derivatives. Despite significant progress in transformation methods of a C-H bond to C-N bonds, a general route for para-selective C-H amination remains elusive. This manuscript reports a new method for para-selective C-H amination of aryl oximes through transient steric control. A preliminary mechanism study revealed