Themed collection Most popular 2019-2020 organic chemistry articles

Intramolecular and intermolecular HAT to C-centered radicals enables selective C–H functionalization of organic molecules.

Efficient radical routes to important alkyl and aryl boronic esters have been developed over the past few years. Such reactions are complementary to existing transition-metal catalysed cross coupling processes.

A range of electroanalytical tools can be applied to studying redox reactions, probing key mechanistic questions in synthetic chemistry.

From carbon fixation, Grignard reaction, metal-catalyzed reactions and asymmetric CO₂-incorporation, what would be the ideal CO₂-functionalization?

A new catalytic method for the direct alkylation of allylic C(sp³)–H bonds from unactivated alkenes via synergistic organo- and photoredox catalysis is described.

By employing an N-heterocyclic carbene (NHC) catalyst, we developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts.

Here we report palladium-catalyzed, regiodivergent [5 + 4] and [5 + 2] annulations of vinylethylene carbonates and allylidenemalononitriles affording over 50 medium-sized heterocycles in high isolated yields with excellent regioselectivities.

Formyl-selective deuteration of aldehydes with D₂O mediated by the synergistic combination of light-driven, polyoxometalate-facilitated HAT and thiol catalysis is reported.

Pd-catalyzed ligand-enabled γ-C(sp³)–H arylation of tert-leucine and its derived peptides without using an external directing group via a less favored six-membered palladacycle is reported.

Amine-anchored sulfamides direct radical-mediated chlorination of aliphatic C–H bonds. The site of C–H abstraction can be modulated by varying the sulfamide nitrogen substituents, a feature that has not been demonstrated with other substrate classes.

Secondary amine selective Petasis (SASP) bioconjugation for the selective labeling of peptides and proteins with N-terminal secondary amines.

We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres.

The mechanism of the gold-catalyzed oxidative cross-coupling of arenes and alkynes has been studied in detail combining stoichiometric experiments with putative reaction intermediates and DFT calculations.

The first general solid-state Suzuki–Miyaura cross-coupling reactions using mechanochemistry has been developed.

A divergent strategy for the remote arylation, vinylation and alkylation of nitriles is described.

The well-known [(TAML)Fe(OH₂)]⁻ complex undergoes proton-coupled oxidation to an Fe-oxo species that supports electrochemical C–H oxidation and alcohol dehydrogenation.

We report first example of template assisted rhodium catalyzed para-C–H alkenylation.

Multicomponent reaction of diazocarbonyl and dibenzenesulfonimide-SCF₃ reagents with BAr₄ salts in the presence of Zn(NTf₂)₂ gives α,α′-difunctionalized trifluoromethylthio compounds.

Minisci alkylation is of prime importance for its applicability in functionalizing diverse heteroarenes, which are core structures in many bioactive compounds.

A general and practical method to directly convert phenols into primary anilines with cheap and easy-to-handle hydrazine as the amine and hydride sources catalyzed by Pd/C.

A reactive ketimine intermediate was demonstrated to be intercepted by a variety of nucleophiles including organometallics and TMSCN.

Herein, we report the radiosynthesis of ¹⁸F-difluoromethylarenes via the assembly of three components, a boron reagent, ethyl bromofluoroacetate, and cyclotron-produced non-carrier added [¹⁸F]fluoride.

An iodine-catalyzed strategy for β C–H amination of alcohols is enabled by a chemo-, regio-, and stereo-selective H-atom transfer mechanism.

A nanogram-to-gram workflow has been established for the identification and development of synthetic transformations which are enabling in Fragment-Based Drug Discovery (FBDD). In this study, we disclose a method for the synthesis of privileged sp²–sp³ architectures via direct cross-dehydrogenative coupling of heterocycles.

A modular synthesis of enantioenriched polyfunctionalized cyclobutanes was developed and applied to the synthesis of (+)-rumphellaone A.

Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature.

A radical relay strategy has been developed to enable selective δ C–H arylation. The approach employs a chiral copper catalyst, which serves the dual roles of generating an N-centered radical to promote intramolecular H-atom transfer, and then intercepting a distal C-centered radical for C–C bond formation with (hetero)aryl boronic acids.

We report an efficient and economical method for remote δ C(sp³)–H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis.

DFT study to elucidate the mechanism of Rh-catalyzed C–H aminations with N-mesyloxycarbamates and the pathway by which by-products formed.

An efficient transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B₂(OH)₄ reagent not only served as the boron source but also acted as an electron donor source through formation of a complex with a DMAc-like Lewis base.