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An isolable pyridinium trifluoromethoxide salt is prepared from the reaction of 4-dimethylaminopyridine with the commercially available liquid 2,4-dinitro(trifluoromethoxy)benzene. The salt is an...

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)–F bonds. Despite many recent advances, a long-standing limitation of these transformations is...

The reaction of carboxylic acid derivatives with amines to form amide bonds has been the most widely used transformation in organic synthesis over the past century. Its utility is driven by the broad...

This report describes the development of a visible-light photocatalytic system for C(sp2)–H amination that leverages in situ-generated photocatalysts. We demonstrate that the combination of acridine...

We are proud to announce Professor Melanie Sanford as the Catalysis in Organic Chemistry Award winner 2020. Read their full profile and share their achievement here.

This Article demonstrates a mild oxidatively induced C(sp3)–H activation at a high-valent Ni center. In contrast with most C(sp3)–H activation reactions at NiII, the transformation proceeds at room...

This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products....

The treatment of pyridine- and pyrazole-ligated NiII σ-aryl complexes with Selectfluor results in C(sp2)–F bond formation under mild conditions. With appropriate design of supporting ligands,...

We use a ligand design strategy to isolate a cyclometalated nickel(IV) complex that is directly analogous to a key intermediate proposed in aminoquinoline-directed C–H functionalization catalysis....

This Article describes the synthesis and characterization of cyclometalated aminoquinoline NiII σ-aryl and σ-alkyl complexes that have been proposed as key intermediates in Ni-catalyzed C–H functio...

This report describes a detailed study of Ni phosphine catalysts for the Suzuki–Miyaura coupling of dichloropyridines with halogen-containing (hetero)aryl boronic acids. With most phosphine ligands,...

ConspectusThe identification of reliable, general, and high yielding methods for the formation of C(sp2)–fluorine bonds remains a major challenge for synthetic organic chemists. A very common...

Nonaqueous redox flow batteries (RFBs) represent a promising technology for grid-scale energy storage. A key challenge for the field is identifying molecules that undergo reversible redox reactions...

This report describes the development of a nickel-catalyzed decarbonylative reaction for the synthesis of fluoroalkyl thioethers (RFSR) from the corresponding thioesters. Readily available, inexpen...

This report describes the synthesis of model complexes for key intermediates in the Pd-catalyzed transannular C(sp3)–H arylation of alicyclic amines. These complexes react stoichiometrically with...

A method for the room temperature deoxyfluorination of benzaldehydes and α-ketoesters using sulfuryl fluoride and Me4NF is described. A large scope of aryl and heteroaryl substrates is demonstrated,...

Over the past decade, numerous reports have focused on the development and applications of Cu-mediated C–H functionalization reactions; however, to date, little is known about the Cu intermediates...

This communication describes the synthesis of a series of diphosphine NiII(Ph)(CF3) complexes and studies of their reactivity toward oxidatively induced Ph–CF3 bond-forming reductive elimination....

This report describes the reactions between N-heterocyclic carbene copper(I) fluoroalkyl complexes and aryl halides bearing ortho-directing groups. Pyridine, pyrazole, oxazoline, imine, and ester...

This Letter describes the development of a TiIII-mediated reaction for the C–H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates,...

This Communication describes the Pd-catalyzed C(sp3)–H functionalization of a tropane derivative to generate products with functionalization at two (β/γ) or three (β/γ/β) different sites on the...

We leverage the photoexcitation of arene–pyridinium electron donor–acceptor (EDA) complexes to achieve C(sp2)−H pyridination. Black light irradiation of the simple combination of arene substrate,...

A palladium-catalyzed cross-coupling of aryl chlorides/bromides with TMSCF2H is described. Two different catalysts, Pd(dba)2/BrettPhos and Pd(PtBu3)2, are demonstrated and provide a variety of...

This communication presents a new preparation for complexes of the general structure [CpRRhCl2]2 (CpR = a substituted cyclopentadienyl ligand). Using isopropyl alcohol as the solvent in place of...