Narrow-band photochemistry and acid cleanly transform six-membered rings into five-membered rings by carbon excision.

Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing...

Selective functional group interconversions in complex molecular settings underpin many of the challenges facing modern organic synthesis. Currently, a privileged subset of functional groups domina...

Highly strained cage hydrocarbons have long stood as fundamental molecules to explore the limits of chemical stability and reactivity, probe physical properties, and more recently as bioactive...

Selectivity in organic chemistry is generally presumed to arise from energy differences between competing selectivity-determining transition states. However, in cases where static density functional...

The intermolecular cleavage of C–C bonds is a rare event. Herein, we report on a late transition-metal terminal nitrido complex, which upon oxidation undergoes insertion of the nitrido nitrogen atom...

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds,...

An osmium nitride is shown to insert nitrogen into indenes to afford isoquinolines. A synthetic cycle to regenerate the starting nitride is presented alongside mechanistic studies of each step.

Given the ubiquity of heterocycles in biologically active molecules, transformations with the capacity to modify such molecular skeletons with modularity remain highly desirable. Ring expansions that...

Advances in site-selective molecular editing have enabled structural modification on complex molecules. However, thus far, their applications have been restricted to C–H functionalization chemistry....

As an important elementary step in organometallic chemistry, the alkylation reaction of palladacycle complexes and alkyl halides has attracted much attention in recent years due to their presence as...

We report an iodoarene-catalyzed enantioselective synthesis of β,β-difluoroalkyl bromide building blocks. The transformation involves an oxidative rearrangement of α-bromostyrenes, utilizing HF–pyr...

The use of a simple stilbene ligand has enabled a stereospecific Suzuki–Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs...

N-oxyl radicals of various structures were generated by oxidation of corresponding N-hydroxy compounds with iodobenzene diacetate, [bis(trifluoroacetoxy)]iodobenzene, and ammonium cerium(IV) nitrate...

Nature - An explosion of skeletal editing methods to insert, delete or swap individual atoms in molecular backbones could accelerate drug discovery.

Reagent inspired by decades-old research could save chemists a lot of headache when it comes to modifying molecules' skeleton

Nature - A study demonstrates that nitrous oxide can act as the source of O in a catalytic conversion of aryl halides to phenols, releasing N2 as by-product.

An interdisciplinary course called “The Chemistry of Poisons” was created, featuring organic chemistry, biology, pharmacology, and toxicology content. This exploratory chemistry elective course was...

Nature - Various rare sugars that cannot be isolated from natural sources are synthesized using light-driven epimerization, a process which may find application in other synthetic scenarios.

Reimagined 19th-century method could potentially take advantage of more than 1,600 commercially available reagents

Metastases to the brain remain a significant problem in lung cancer, as treatment by most small-molecule targeted therapies is severely limited by efflux transporters at the blood–brain barrier...

The discovery of catalytic systems based on earth-abundant transition metals for the functionalization of C–H bonds enables streamlined and sustainable solutions to problems in synthetic organic...

Dibenzo-7-phosphanorbornadiene-substituted diazene MesN2PA (1, where Mes = mesityl, A = anthracene, or C14H10), a synthetic equivalent of mesitylphosphaazide (MesN2P) and anthracene, was synthesized...

Several perfluoroalkylcopper compounds have been reported previously that serve as reagents or catalysts for the perfluoroalkylation of aryl halides. However, the relationships between the reactivity...

With researchers back in the swing of things, we review the year’s top trends, fascinating findings, memorable molecules, and more

A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator...