Themed collection 2023 Organic Chemistry Frontiers HOT articles
New Advances in Chiral Nanographene Chemistry
Applications of trisulfide radical anion S3˙− in organic synthesis
The synthetic and mechanistic aspects of the role of the trisulfide radical anion S3˙− in organic chemistry are reviewed.
Recent progress on the chemical synthesis of bacterial non-2-ulosonic acids
Recent advances in intramolecular kinetic resolution reactions
Electrochemical synthesis and transformation of organoboron compounds
This review highlights the recent advances in both electrochemical borylation and hydroboration to synthesize organoboron compounds and electrochemical transformation of organoboron compounds to construct carbon–carbon and carbon–heteroatom bonds.
Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds
Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds and their mechanistic insights and synthetic applications have been summarized.
Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism
This review summarizes the recent advances in cyclization reactions involving pyridinium 1,n-zwitterions (n = 4 and 5) and highlights the applications of pyridinium 1,n-zwitterions (n = 4 and 5) in the efficient construction of heterocycles.
Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species
This review summarizes a view of the advances in the catalytic asymmetric α-functionalization of vinylogous nucleophilic species, the content of which is categorized based on the type of vinylogous donor.
Recent advances in the asymmetric catalytic construction of oxa-quaternary carbon centers
This review focuses on the very recent advances (from 2020 to the beginning of 2023) in enantioselective catalytic reactions for the construction of oxa-quaternary stereocenters.
Artemeriopolides A–D, two types of sesquiterpenoid dimers with rare carbon skeletons from Artemisia eriopoda and their antihepatoma cytotoxicity
Artemeriopolides A–D (1–4), four novel cadinane sesquiterpenoid dimers featuring the rare 2-oxaspiro[4.6]undecan-1,7-dione, 2-oxaspiro[4.5]decan-1-one, and 2-oxaspiro[5.5]undecan-1-one ring systems, were isolated from Artemisia eriopoda.
DFT study on stereoselective Rh-catalyzed intramolecular [2 + 2 + 2] cycloaddition of allene–ene–ynes
CAT catalyzes the reaction of 1a to generate intermediate INT2, which is a common intermediate to generate final products 2a and 3a.
Transition metal-free and regioselective alkenyl C–S cross-coupling reaction of alkenylsulfonium salts
A novel and highly efficient strategy for the construction of diverse alkenyl sulfoxides via transition metal-free C–S cross-coupling of sulfenate anions with alkenylsulfonium salts is reported.
2,7-Dinitrophenanthrene-9,10-dione as a photosensitizer for the dehydrogenative lactonization of 2-arylbenzoic acids
This report describes the visible-light-induced C–H/COO–H oxidative coupling reaction of 2-arylbenzoic acids to synthesize benzo-3,4-coumarins by using 2,7-dinitrophenanthrene-9,10-dione as a photocatalyst.
Catalytic asymmetric [4 + 1] cycloaddition to synthesize chiral pyrazoline-spirooxindoles
The first asymmetric [4 + 1] annulation of oxindole 3-pyridinium salts and hydrazones is realized by using a chiral N,N′-dioxide-Pr(OTf)3 complex. A range of bioactive chiral pyrazoline-spirooxindoles are obtained in good yields with excellent ee values.
Regio- and stereoselective oxidative conversion of alkynes to sulfenylated α,β-unsaturated carbonyls
An electrophilic sulfenylation promoted oxidation of alkynes is presented, providing the chemo-, regio- and stereoselective synthesis of α-sulfenylated α,β-unsaturated aldehydes.
Visible light mediated regioselective 1,3-oxylallylation of aryl cyclopropanes under redox-neutral conditions
A photoredox catalysed 1,3-oxylallylation of aryl cyclopropanes was accomplished by reaction with carboxylic acids and allyl sulfones.
Chiral oxalamide phosphine (COAP)-Pd-catalyzed enantioselective cascade formal [4 + 1] annulation for enantioenriched 2,3-disubstituted indolines and further DFT study on regio- and stereocontrol
COAP-Pd-catalyzed asymmetric cascade formal [4 + 1] annulation was developed between racemic vinyl benzoxazinones and N-tosylhydrazone sodium salts, affording trans-2,3-disubstituted indolines in good yields with high stereoselectivity.
Carboxylic acid-assisted sterically demanding reductive cross-coupling between cycloalkenyl and alkyl bromides
Carboxylic acid-assisted sterically demanding reductive cross-coupling between cycloalkenyl and alkyl bromides affords all-carbon tetrasubstituted cycloalkenes under mild reaction conditions in good yields.
Copper(I)-catalyzed multicomponent interrupted click reaction: modular synthesis of triazole sulfides from elemental sulfur
A new multicomponent copper(I)-catalyzed interrupted click reaction which allows the rapid modular synthesis of multisubstituted triazole sulfides including various medium-sized and macrocycles in one-step from elemental sulfur was reported.
Photocatalytic dehydrations for the Ritter reaction
A photocatalytic dehydration method was developed to efficiently convert benzyl alcohols to the corresponding amides.
Construction of methylene-bridged electron-deficient corona[n]arenes and selective fluoride recognition through anion–π interactions
Despite significant development of the nascent anion–π interactions in recent years, the noncovalent interactions between fluoride ion, a unique anion species, and electron-neutral aromatic rings remain rare and even controversial.
Bis(pentafluorophenyl)borane-catalyzed E-selective isomerization of terminal alkenes to internal alkenes
The bis(pentafluorophenyl)borane-catalyzed E-selective isomerization of terminal alkenes to internal alkenes via a hydroboration/retro-hydroboration sequence is reported.
HTE and machine learning-assisted development of iridium(I)-catalyzed selective O–H bond insertion reactions toward carboxymethyl ketones
By combining HTE and machine learning technologies, an iridium(I)-catalyzed highly selective O–H bond insertion reaction of carboxylic acids and sulfoxonium ylides was developed, and an extensive reaction space exploration was accomplished.
Photoredox-catalyzed sequential Dowd–Beckwith ring expansion and C–H functionalization of THIQs
An efficient tandem Dowd–Beckwith ring expansion/C–H functionalization of tetrahydroisoquinoline (THIQ) is disclosed upon photocatalysis, which provided a unique thought to connect important medium-sized cycloalkanones with THIQs skeletons together.
Mechanistic study of nickel-catalyzed intramolecular [4 + 2] cycloaddition of cyclobutanone with allene: origin of selectivity and ligand effect
The transition metal catalyzed cycloaddition reaction is one of the most powerful tools for the construction of carbon- and heterocycles. DFT studies are performed to investigate the mechanism of the Ni-catalyzed intramolecular [4 + 2] cycloaddition.
Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling
Visible light-mediated NHC and photoredox co-catalyzed radical 1,2-sulfonylacylation of allenes via cross-coupling between an allyl radical and an NHC-stabilized acyl radical.
Photoredox-catalyzed intermolecular azidosulfonylation of alkenes with DABCO·(SO2)2, trimethylsilyl azide and thianthrenium salts
Synthesis of β-azido alkylsulfones through a photoredox-catalyzed azido sulfonylation of alkenes with DABCO·(SO2)2, trimethylsilyl azide and alkyl thianthrenium salts is developed.
Photo-induced redox cascade reaction of nitroarenes and amines
A photo-induced redox cascade reaction has been developed for the chemoselective construction of isoxazolidine derivatives from stable and easily available nitroarenes and amines.
Divergent synthesis of quinoxalin-2(1H)-one derivatives through photoinduced C–H functionalization without a photocatalyst
Photo-induced C–H functionalization for divergent synthesis of quinoxalin-2(1H)-one derivatives using H2O2 as an oxidant without a photocatalyst.
In situ generated aminodiborane as a reagent for deoxygenative reduction of carboxamides to amines
The in situ generated aminodiborane (μ-NH2B2H5) using NH3BH3 and elemental iodine (I2) is used for the reduction of carboxamides to amines.
An organic photoredox catalyst promoted para-selective C–H amination of aryl oximes
Direct C–H amination methods are essential because of the importance of aryl amine derivatives.
Cr-catalyzed chiral allenone synthesis via sequential radical–polar crossover and Oppenauer oxidation
We describe the Cr-catalyzed enantioconvergent synthesis of chiral 2,3-allenones from aldehydes and propargyl bromides, which features an unprecedented cascade of Cr-catalyzed asymmetric reductive radical–polar crossover and Oppenauer oxidation.
Supramolecular vesicle engineering by regulating the assembly of shape-persistent aromatic-hydrazone macrocycles
The size of supramolecular vesicles is manipulated by regulating the assembly of macrocycles with different mono- or bi-pyridinium salts.
Ring-expansion from tellurophenes to telluropyrans: inhibition of C–Te bond cleavages in transition metal-catalyzed reactions
Telluropyran derivatives have been facilely synthesized via a ring-expansion cyclization from the corresponding tellurophene compounds and their conjugation can be extended via various transition metal-catalyzed coupling reactions.
Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality
Organocatalytic enantioselective construction of chiral spiro N,N-acetal carbon stereocenters and axially chiral 3-arylindoles has been achieved in one pot.
Dual nickel/photoredox catalyzed carboxylation of C(sp2)-halides with formate
A novel and practical strategy for the dehalocarboxylation of C(sp2)-halides with formate via visible-light photoredox nickel dual catalysis was disclosed.
Precise control of the site selectivity in ruthenium-catalyzed C–H bond amidations using cyclic amides as powerful directing groups
A ruthenium-catalyzed C–H amidation using cyclic amides as directing groups features broad functional group tolerance. Mechanistic studies supported by DFT calculations highlight the relevance of six-membered ruthenacycles in the catalytic cycle.
Versatile access to nitrogen-rich π-extended indolocarbazoles via a Pictet–Spengler approach
A bidirectional Pictet-Spengler Reaction allows easy access to nitrogen-rich aromatics with seven fused rings. Photophysical measurements and computational methods show significant differences to parent N-heteropolycycles with fewer nitrogen atoms.
About this collection
Read our on-going collection of the hottest research published as advanced article from Organic Chemistry Frontiers in 2023. These articles are recommended by reviewers as being of significant novelty and interest. Congratulations to all the authors whose articles are featured!