Themed collection 2021 Organic Chemistry Frontiers HOT articles
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Metal-free synthesis of N-sulfonylformamidines via skeletal reconstruction of sulfonyl oximonitriles
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.
Org. Chem. Front., 2022,9, 627-632
https://doi.org/10.1039/D1QO01665B
Photoredox-catalyzed synthesis of sulfonated oxazolines from N-allylamides through the insertion of sulfur dioxide
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.
Org. Chem. Front., 2022,9, 364-369
https://doi.org/10.1039/D1QO01540K
Synthesis of amidines via iron-catalyzed dearomative amination of β-naphthols with oxadiazolones
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.
Org. Chem. Front., 2022,9, 380-385
https://doi.org/10.1039/D1QO01687C
Insight into the mechanism of the arylation of arenes via norbornene relay palladation through meta- to para-selectivity
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.
Org. Chem. Front., 2022,9, 129-139
https://doi.org/10.1039/D1QO01500A
Construction of polysubstituted spiro[2.3] or [3.3] cyclic frameworks fused with a tosylated pyrrolidine promoted by visible-light-induced photosensitization
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.
Org. Chem. Front., 2021,8, 6823-6829
https://doi.org/10.1039/D1QO01373D
Design of chiral ferrocenylphosphine-spiro phosphonamidite ligands for ruthenium-catalyzed highly enantioselective coupling of 1,2-diols with amines
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.
Org. Chem. Front., 2021,8, 6830-6836
https://doi.org/10.1039/D1QO01443A
Visible-light photocatalytic preparation of alkenyl thioethers from 1,2,3-thiadiazoles and Hantzsch esters: synthetic and mechanistic investigations
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.
Org. Chem. Front., 2021,8, 6499-6507
https://doi.org/10.1039/D1QO01076J
Janthinoid A, an unprecedented tri-nor-meroterpenoid with highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold, produced by the endophyte of Penicillium janthinellum TE-43
Janthinoid A (1), an unprecedented C22 meroterpenoid featuring a highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold, was produced by Penicillium janthinellum.
Org. Chem. Front., 2021,8, 6196-6202
https://doi.org/10.1039/D1QO01066B
A robust and facile method for desulfonation to amines
In this study, a robust and facile method for desulfonation to achieve secondary amines is demonstrated.
Org. Chem. Front., 2021,8, 6182-6186
https://doi.org/10.1039/D1QO01190A
Controllable Z/E-selective synthesis of α-amino-ketoximes from N-nitrososulfonamides and aryl alkenes under neutral conditions
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.
Org. Chem. Front., 2021,8, 5785-5792
https://doi.org/10.1039/D1QO01101D
Cunlanceloic acids A–D: unprecedented labdane diterpenoid dimers with AChE inhibitory and cytotoxic activities from Cunninghamia lanceolata
Four unprecedented labdane diterpenoid dimers with new carbon skeletons, cunlanceloic acids A–D (1–4), were isolated from the cones of Cunninghamia lanceolata.
Org. Chem. Front., 2021,8, 5777-5784
https://doi.org/10.1039/D1QO00999K
A supramolecular dual-donor artificial light-harvesting system with efficient visible light-harvesting capacity
A supramolecular dual-donor artificial light-harvesting system with efficient visible light-harvesting capacity was constructed through the hierarchical self-assembly approach.
Org. Chem. Front., 2021,8, 5250-5257
https://doi.org/10.1039/D1QO00771H
Amide-assisted α-C(sp3)–H acyloxyation of organic sulfides to access α-acyloxy sulfides
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.
Org. Chem. Front., 2021,8, 4974-4979
https://doi.org/10.1039/D1QO00774B
Rh(III)-Catalyzed one-pot three-component cyclization reaction: rapid selective synthesis of monohydroxy polycyclic BINOL derivatives
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.
Org. Chem. Front., 2021,8, 4967-4973
https://doi.org/10.1039/D1QO00779C
Expanded all-phenylene molecular spoked wheels: cutouts of graphenylene-3
All-phenylene molecular spoked wheels, cutouts of graphenylene-3, have been synthesized by intramolecular Yamamoto coupling of the respective dodecabromides.
Org. Chem. Front., 2021,8, 4980-4985
https://doi.org/10.1039/D1QO00876E
A multi-responsive supramolecular heparin-based biohybrid metallogel constructed by controlled self-assembly based on metal–ligand, host–guest and electrostatic interactions
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.
Org. Chem. Front., 2021,8, 4715-4722
https://doi.org/10.1039/D1QO00692D
Facile and practical hydrodehalogenations of organic halides enabled by calcium hydride and palladium chloride
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.
Org. Chem. Front., 2021,8, 4685-4692
https://doi.org/10.1039/D1QO00758K
Access to diverse primary, secondary, and tertiary amines via the merger of controllable cleavage of triazines and site-selective functionalization
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.
Org. Chem. Front., 2021,8, 4706-4714
https://doi.org/10.1039/D1QO00883H
Organocatalytic electrochemical amination of benzylic C–H bonds
An organocatalytic site-selective electrochemical method for the benzylic C–H amination of alkylarenes with azoles through hydrogen evolution has been developed.
Org. Chem. Front., 2021,8, 4700-4705
https://doi.org/10.1039/D1QO00746G
Truxene-based covalent organic polyhedrons constructed through alkyne metathesis
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.
Org. Chem. Front., 2021,8, 4723-4729
https://doi.org/10.1039/D1QO00685A
Enantiopure isothiourea@carbon-based support: stacking interactions for recycling a lewis base in asymmetric catalysis
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.
Org. Chem. Front., 2021,8, 4693-4699
https://doi.org/10.1039/D1QO00646K
Nine sesquiterpenoid dimers with four unprecedented types of carbon skeleton from Chloranthus henryi var. hupehensis
Chlorahupetones A–I (1–9), nine sesquiterpenoid dimers, were isolated from Chloranthus henryi var. hupehensis.
Org. Chem. Front., 2021,8, 4374-4386
https://doi.org/10.1039/D1QO00810B
Diastereoselective synthesis of functionalized tetrahydropyridazines containing indole scaffolds via an inverse-electron-demand aza-Diels–Alder reaction
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.
Org. Chem. Front., 2021,8, 4392-4398
https://doi.org/10.1039/D1QO00623A
Visible-light-induced radical cascade cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfonyl chlorides for the synthesis of sulfonated benzoxepines
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.
Org. Chem. Front., 2021,8, 4095-4100
https://doi.org/10.1039/D1QO00611H
Photoinitiated stereoselective direct C(sp2)–H perfluoroalkylation and difluoroacetylation of enamides
Photoinitiated regio- and stereoselective C(sp2)–H perfluoroalkylation and difluoroacetylation of enamides are developed, furnishing biologically and physiologically privileged fluoro-containing enamide scaffolds.
Org. Chem. Front., 2021,8, 4086-4094
https://doi.org/10.1039/D1QO00605C
An unusual reaction mode of 1-phenylpyrazolidinones toward diazonaphthalen-2(1H)-ones featuring cascade C(sp2)–H and C(sp3)–H bond cleavage
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.
Org. Chem. Front., 2021,8, 3238-3243
https://doi.org/10.1039/D1QO00305D
Engaging DBFO as a C1N1 “two-atom synthon” in [3 + 2] cycloaddition reaction: synthesis of the energetic material 5-azidotetrazolate 1N-oxide
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.
Org. Chem. Front., 2021,8, 2420-2428
https://doi.org/10.1039/D1QO00123J
Palladium-catalyzed 1,2-amino carbonylation of 1,3-dienes with (N-SO2Py)-2-iodoanilines: 2,3-dihydroquinolin-4(1H)-ones synthesis
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.
Org. Chem. Front., 2021,8, 2429-2433
https://doi.org/10.1039/D1QO00290B
Enantioselective modification of sulfonamides and sulfonamide-containing drugs via carbene organic catalysis
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.
Org. Chem. Front., 2021,8, 2413-2419
https://doi.org/10.1039/D1QO00212K
Pd/LA-catalyzed decarboxylation enabled exclusive [5 + 2] annulation toward N-aryl azepanes and DFT insights
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.
Org. Chem. Front., 2021,8, 1902-1909
https://doi.org/10.1039/D1QO00070E
Dearomative 1,6-addition of P(O)–H to in situ formed p-QM-like ion pairs from 2-benzofuryl-ols to C3-phosphinoyl hydrobenzofurans
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.
Org. Chem. Front., 2021,8, 1756-1763
https://doi.org/10.1039/D1QO00076D
Merging radical-polar crossover/cycloisomerization processes: access to polyfunctional furans enabled by metallaphotoredox catalysis
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.
Org. Chem. Front., 2021,8, 1732-1738
https://doi.org/10.1039/D0QO01472A
Rhodium-catalyzed enone carbonyl directed C–H activation for the synthesis of indanones containing all-carbon quaternary centers
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.
Org. Chem. Front., 2021,8, 1447-1453
https://doi.org/10.1039/D1QO00056J
Rhodium-catalyzed annulation of pyrrole substituted BODIPYs with alkynes to access π-extended polycyclic heteroaromatic molecules and NIR absorption
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.
Org. Chem. Front., 2021,8, 868-875
https://doi.org/10.1039/D0QO01625J
Thermodynamic and kinetic studies of hydride transfer from Hantzsch ester under the promotion of organic bases
Thermodynamics and kinetics for base-promoted hydride transfer (BPHyT) were investigated with Hantzsch ester and acridinium derivatives as model compounds.
Org. Chem. Front., 2021,8, 876-882
https://doi.org/10.1039/D0QO01478H
About this collection
Read our on-going collection of the hottest research published as advanced article from Organic Chemistry Frontiers in 2021. These articles are recommended by reviewers as being of significant novelty and interest. Congratulations to all the authors whose articles are featured!