Themed collection 2021 Organic Chemistry Frontiers HOT articles

We firstly develop an unprecedented domino reaction of sulfonyl oximonitriles with secondary amines to streamline synthesis of N-sulfonylformamidines in decent to high yields under mild reaction conditions.

Photoredox-catalyzed generation of sulfonated oxazolines starting from N-allylamides, DABCO·(SO₂)₂, and aryldiazonium salts has been developed and a range of sulfonated oxazolines were obtained in moderate to good yields.

An efficient and convenient method for the synthesis of amidines bearing a β-naphthalenone moiety catalyzed by cheap iron(II) chloride is presented by employing oxadiazolones as the nitrene precursors.

A theoretical insight was shown into the origin of site-selectivity in the arylation of arenes by a norbornene relay palladation through meta- to para-selectivity.

A novel visible-light-induced intramolecular [2 + 2] cycloaddition of methylenecyclopropanes (MCPs) for the rapid construction of polysubstituted spiro[2.3] or [3.3] cyclic frameworks fused with a tosylated pyrrolidine.

A series of chiral ferrocene-backbone phosphines-spiro phosphonamidite ligands was developed for ruthenium-catalyzed enantioselective access to a broad range of β-amino alcohols from 1,2-diols and amines via the borrowing-hydrogen prciniple.

A visible-light-promoted S-alkylation of 1,2,3-thiadiazoles with C-radical precursors, 4-alkyl-1,4-dihydropyridines (DHPs), to produce alkenyl thioethers is disclosed.

Janthinoid A (1), an unprecedented C₂₂ meroterpenoid featuring a highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold, was produced by Penicillium janthinellum.

In this study, a robust and facile method for desulfonation to achieve secondary amines is demonstrated.

An amidoximation of alkenes with N-nitrososulfonamides enabled by triplet energy transfer under neutral conditions is presented. Both (Z)- and (E)-α-amino-ketoximes are selectively accessible depending on the triplet energy of the photosensitizer.

Four unprecedented labdane diterpenoid dimers with new carbon skeletons, cunlanceloic acids A–D (1–4), were isolated from the cones of Cunninghamia lanceolata.

A supramolecular dual-donor artificial light-harvesting system with efficient visible light-harvesting capacity was constructed through the hierarchical self-assembly approach.

The direct acyloxyation of 2-(alkylthio)benzamide has been established via an amide-assisted α-C(sp³)–H functionalization in the presence of Selectfluor by using simple carboxylic acid and its corresponding salt as acyloxy sources.

A Rh(III)-catalyzed three-component C–H bond functionalization protocol has been successfully applied to access complex polycyclic BINOL derivatives in which the formation of intermediate amides occurred in situ from aldehydes and amines.

All-phenylene molecular spoked wheels, cutouts of graphenylene-3, have been synthesized by intramolecular Yamamoto coupling of the respective dodecabromides.

A new family of supramolecular heparin-based biohybrid metallogels with multiple stimuli-responsive behaviours was constructed through the controlled self-assembly based on three orthogonal interactions within a single system.

For the first time, calcium hydride and palladium chloride were used to reduce a wide range of organic halides including aromatic bromides, aromatic chlorides, aromatic triflates, aliphatic bromides, aliphatic chlorides and trihalomethyl compounds.

An efficient approach for divergent synthesis of primary, secondary, and tertiary amines via the merger of controllable cleavage of triazines and site-selective functionalization is disclosed.

An organocatalytic site-selective electrochemical method for the benzylic C–H amination of alkylarenes with azoles through hydrogen evolution has been developed.

Dynamic alkyne metathesis has successfully been employed toward the synthesis of a truxene-based shape-persistent covalent organic polyhedron (COP) with high binding affinity for fullerenes.

An enantiopure isothiourea (hyperBTM) was functionalized by a pyrene moiety via click chemistry; immobilized on reduced Graphene Oxide, this recyclable chiral organocatalyst promotes formal [3+2] cycloaddition of ammonium enolates with oxaziridines.

Chlorahupetones A–I (1–9), nine sesquiterpenoid dimers, were isolated from Chloranthus henryi var. hupehensis.

A base-promoted and catalyst-free unprecedented inverse-electron-demand aza-Diels–Alder reaction between the in situ generated azoalkenes and 3-vinylindoles has been developed to afford tetrahydropyridazines containing indole scaffolds.

A visible light photocatalyzed cascade sulfonylation/cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfonyl chlorides for the construction of sulfonated benzoxepines is developed.

Photoinitiated regio- and stereoselective C(sp²)–H perfluoroalkylation and difluoroacetylation of enamides are developed, furnishing biologically and physiologically privileged fluoro-containing enamide scaffolds.

Herein, a novel synthesis of pyrazolidinone fused 1,3-benzooxazepine derivatives via a formal [4 + 3] annulation reaction of 1-phenylpyrazolidinones with diazonaphthalen-2(1H)-ones is presented.

Employing 1,1-dibromoformaloxime as a novel C1N1 “two-atom synthon” for the synthesis of tetrazole-based energetic materials via an intramolecular [3 + 2] annulation in aqueous solution.

A palladium-catalyzed 1,2-amino carbonylation of 1,3-dienes with (N-SO₂Py)-2-iodoanilines has been developed for the construction of 2,3-dihydroquinolin-4(1H)-one scaffolds.

Enantioselective modification of sulfonamides and sulfonamide-containing drugs via carbene organic catalysis is disclosed. The cation−π interaction was computationally found to play a pivotal role in modulating the reaction enantioselectivity.

A practical approach towards the synthesis of non-fused N-aryl azepane derivatives with diversity is described. DFT calculations revealed the origins of this unusual exclusive [5 + 2] rather than empirical [3 + 2] annulation process.

We report a dearomative C3-phosphorylation and a tandem C3-phosphorylation/aromatization of 2-benzofuryl-ols with P(O)–H species to afford C3-phosphinoyl hydrobenzofurans and benzofurans, respectively.

Metallaphotoredox catalysis for furan synthesis: The cyclisation of yne-enones proceeds smoothly via consecutive reductive radical-polar crossover and cycloisomerization processes enabled by cooperative photoredox-neutral and copper catalysis.

Rhodium(III)-catalyzed enone carbonyl directed C–H activation/annulation of α-aroyl ketene dithioacetals with diazo compounds has been realized for the synthesis of β-quaternary indanones.

A series of π-extended BODIPY derivatives fused with an indolizine scaffold were prepared smoothly via rhodium-catalyzed C–H functionalization/annulation. These fluorophores show significantly red-shifted absorption, reaching to the near infrared (NIR) region.

Thermodynamics and kinetics for base-promoted hydride transfer (BPHyT) were investigated with Hantzsch ester and acridinium derivatives as model compounds.