Themed collection 2022 Organic Chemistry Frontiers HOT articles
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Rational design of arsine catalysts for arsa-Wittig reaction
An acyclic arsine catalyst has been developed for the room-temperature catalytic arsa-Wittig reaction. The reaction mechanism has been computationally analyzed.
Org. Chem. Front., 2022,9, 6786-6794
https://doi.org/10.1039/D2QO01480G
Unusual DBU-catalyzed decarboxylative formation of allylic thioethers from vinyl cyclic carbonates and thiols
Vinyl cyclic carbonates undergo an exo-cyclic attack by thiol nucleophiles under DBU catalysis to form allylic thioether products in moderate to good yields through a decarboxylative process under attractive process conditions.
Org. Chem. Front., 2022,9, 6780-6785
https://doi.org/10.1039/D2QO01511K
Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines
We herein report an efficient and green aerobic radical cascade reaction of o-vinylphenylisocyanides with thiols to access a broad range of 2-thio-substituted quinolines without the need for additional catalysts or oxidants.
Org. Chem. Front., 2022,9, 6484-6489
https://doi.org/10.1039/D2QO01371A
Formamidation of a wide range of substituted and functionalized amines with CO and a base
We have developed a base mediated formamidation of amines with CO under mild conditions, which allows for the synthesis of a wide range of aromatic and aliphatic formamides in high yields and gram amounts in the absence of a transition metal.
Org. Chem. Front., 2022,9, 6142-6148
https://doi.org/10.1039/D2QO01312F
Palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones: development and application to the synthesis of (+)-herbertene-1,14-diol
A palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones is reported, providing chiral 1-indanones bearing a versatile alkenyl group.
Org. Chem. Front., 2022,9, 5798-5801
https://doi.org/10.1039/D2QO01239A
Cobalt-catalyzed highly selective hydroxylation of organohydrosilanes and hydrosiloxanes
The highly selective and scalable dehydrogenative hydroxylation of hydrosilanes, featuring a low loading of the Earth-abundant cobalt catalyst, water as the green oxidant, and good generality for various hydrosilanes, is reported.
Org. Chem. Front., 2022,9, 5802-5807
https://doi.org/10.1039/D2QO01294D
Visible-light enabled synthesis of cyclopropane-fused indolines via dearomatization of indoles
An efficient synthesis of methylene-unsubstituted cyclopropane-fused indolines via photoredox catalyzed dearomative cyclopropanation of indole derivatives was developed.
Org. Chem. Front., 2022,9, 5463-5468
https://doi.org/10.1039/D2QO01174C
Charge transfer complex enabled photoreduction of Wittig phosphonium salts
An efficient photoactive charge transfer complex protocol for the (alkoxycarbonyl)methylation reaction of alkenes with phosphonium salts is established.
Org. Chem. Front., 2022,9, 5469-5472
https://doi.org/10.1039/D2QO01079H
(3 + 2)-Annulation of 1,3-N,Si-tetraorganosilane reagents TsHNCH2SiBnR1R2 with arynes for efficient synthesis of 3-silaindolines
1,3-N,Si-Tetraorganosilane reagents TsHNCH2SiBnR1R2 were developed as robust synthons to prepare 3-silaindolines via a Cs2CO3-promoted (3 + 2)-annulation reaction with arynes.
Org. Chem. Front., 2022,9, 5453-5462
https://doi.org/10.1039/D2QO01075E
The cobalt(II)-catalyzed acyloxylation of picolinamides with bifunctional silver carboxylate via C–H bond activation
The cobalt(II)-catalyzed C–H bond acyloxylation of picolinamides with bifunctional silver carboxylate has been developed. The mild and practical esterification provides an atom-economic route to access to polysubstituted naphthalene compounds.
Org. Chem. Front., 2022,9, 5125-5132
https://doi.org/10.1039/D2QO01131J
Electrochemical enantioselective dihydroxylation reaction of N-alkenyl nucleobases for the construction of chiral acyclic nucleosides
A simple and sustainable KI-mediated electrochemical enantioselective dihydroxylation reaction for the synthesis of chiral acyclic nucleosides was developed for the first time with only a 0.1 mol% Os catalyst.
Org. Chem. Front., 2022,9, 4818-4822
https://doi.org/10.1039/D2QO00971D
Disarming the alkoxide trap to access a practical FeCl3 system for borrowing-hydrogen N-alkylation
Disarming the alkoxide trap using an in situ reduction strategy to access a practical FeCl3 and N-heterocyclic carbene system for borrowing-hydrogen N-alkylation.
Org. Chem. Front., 2022,9, 4803-4817
https://doi.org/10.1039/D2QO00825D
External oxidant-free and selective thiofunctionalization of alkenes enabled by photoredox-neutral catalysis
A photoredox approach was reported to realize a highly selective three-component thiohydroxylation, thioalkoxylation and thioamination of vinylarenes towards valuable vicinal S,O- and S,N-disubstituted molecules under mild conditions.
Org. Chem. Front., 2022,9, 4536-4541
https://doi.org/10.1039/D2QO00957A
Formal total synthesis of dankasterone B
A formal total synthesis of dankasterone B was achieved in 15 steps.
Org. Chem. Front., 2022,9, 3961-3965
https://doi.org/10.1039/D2QO00299J
A nickel(II)-catalyzed enantioselective all-carbon-based inverse-electron-demand Diels–Alder reaction of 2-pyrones with indenes
An asymmetric IEDDA reaction of 2-pyrones with indenes catalyzed by a chiral N,N′-dioxide/Ni(OTf)2 complex has been disclosed to construct highly functionalized hexahydrofluorenyl bridged-lactone scaffolds in high yields and ee.
Org. Chem. Front., 2022,9, 3956-3960
https://doi.org/10.1039/D2QO00493C
Asymmetric living supramolecular polymerization of an achiral aza-BODIPY dye by solvent-mediated chirality induction and memory
Chiral aggregates of achiral aza-BODIPY 1 was obtained in a nearly achiral medium, i.e. a limonene/MCH mixed solvent with a chiral limonene ratio <1% (v/v), by living supramolecular polymerization exploiting the chirality memory of dye 1 aggregates.
Org. Chem. Front., 2022,9, 3949-3955
https://doi.org/10.1039/D2QO00623E
Total synthesis of huperserratines A and B
The first total synthesis of two macrocyclic Lycopodium alkaloids, huperserratines A and B, in 12 steps.
Org. Chem. Front., 2022,9, 3664-3668
https://doi.org/10.1039/D2QO00608A
Metal-free dearomatization reactions of naphthol-ynamides for the divergent and enantioselective synthesis of azaspirocycles
An efficient Brønsted acid (BA) catalyzed intramolecular dearomatization cyclization of naphthol-ynamides has been developed, enabling the practical and divergent synthesis of two azaspirocycles in high yields.
Org. Chem. Front., 2022,9, 3709-3717
https://doi.org/10.1039/D2QO00685E
Momentary click nitrile synthesis enabled by an aminoazanium reagent
By using a robust aminoazanium reagent H2N-DABCO, a momentary clicking nitrile synthesis from aldehyde and various adehyde precursors was achieved.
Org. Chem. Front., 2022,9, 3420-3427
https://doi.org/10.1039/D2QO00560C
Decarboxylative cyclization of o-chlorobenzoic acids with C,C-palladacycles formed by an aminopalladation/dealkylation strategy to access dibenzo[a,c]carbazoles
A novel decarboxylative cyclization of o-chlorobenzoic acids with C,C-palladacycles formed by an aminopalladation/dealkylation strategy for the assembly of dibenzo[a,c]carbazoles has been reported.
Org. Chem. Front., 2022,9, 3414-3419
https://doi.org/10.1039/D2QO00490A
Automated solid phase assisted synthesis of a heparan sulfate disaccharide library
An automated machine-aided solid phase synthesis of heparan sulfate (HS) has been established for the first time. With the significantly reduced number of synthetic and purification steps, 16 HS disaccharides have been readily assembled.
Org. Chem. Front., 2022,9, 2910-2920
https://doi.org/10.1039/D2QO00439A
Transition-metal-free oxindole synthesis: quinone–K2CO3 catalyzed intramolecular radical cyclization
A highly efficient transition-metal-free radical cyclization route for the synthesis of oxindoles was developed, using the readily available 9,10-phenanthrenequinone (PQ) catalyst together with K2CO3.
Org. Chem. Front., 2022,9, 2593-2599
https://doi.org/10.1039/D2QO00205A
Asperflavipines C–E and aspermichalasine A: three cytochalasan heterotetramers and an unusual cytochalasan monomer from Aspergillus micronesiensis
Asperflavipines C–E, three new cytochalasin heterotetramers, possessing a highly complex tetradecacyclic ring system with continuous bridged ring systems, and aspermichalasine A, possessing an unusual 5/6/5/8 ring system, were isolated.
Org. Chem. Front., 2022,9, 2585-2592
https://doi.org/10.1039/D2QO00309K
Total synthesis of monoterpenoid indole alkaloid (–)-arbophyllidine
The first asymmetric total synthesis of (–)-arbophyllidine, an unusual pentacyclic monoterpenoid indole alkaloid, has been achieved.
Org. Chem. Front., 2022,9, 2328-2332
https://doi.org/10.1039/D2QO00284A
Concise total synthesis of opioids
A concise total synthesis of opioids is presented. The development of a regioselective Pd-catalyzed dearomatization arene coupling that requires no additional blocking groups allows for efficient access to a common thebaine core.
Org. Chem. Front., 2022,9, 2322-2327
https://doi.org/10.1039/D2QO00202G
Diastereoselective synthesis of 1,1,3,3-tetrasubstituted cyclobutanes enabled by cycloaddition of bicyclo[1.1.0]butanes
A diastereoselective cycloaddition of bicyclo[1.1.0]butanes (BCBs) with triazolinedione or nitrosoarenes was developed to access multi-substituted cyclobutanes.
Org. Chem. Front., 2022,9, 2149-2153
https://doi.org/10.1039/D2QO00167E
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Controlling rotary motion of molecular motors based on oxindole
We present a new family of oxindole-based functionalised at three positions on the upper and lower halves, with methoxy or cyano groups. We find that this allows the absorption wavelength and quantum yields of these motors to be tuned.
Org. Chem. Front., 2022,9, 2084-2092
https://doi.org/10.1039/D2QO00129B
Co-Catalyzed C(sp3)–C(sp2) bond cleavage via hydrogen atom transfer
A new HAT-initiated C(sp3)–C(sp2) bond cleavage approach enabling the functionalization of alkenes to ketones is presented.
Org. Chem. Front., 2022,9, 2135-2140
https://doi.org/10.1039/D2QO00125J
Access to axially chiral aryl 1,3-dienes by transient group directed asymmetric C–H alkenylations
An enantioselective olefinic C–H alkenylation using transient group was disclosed to afford axially chiral aryl 1,3-dienes in up to 99% yields and up to >99% ee. The derived carboxylic acid was efficient ligand in asymmetric C–H alkylation.
Org. Chem. Front., 2022,9, 2109-2115
https://doi.org/10.1039/D2QO00161F
Unimolecular cooperative metallaphotocatalysis with conjugately bridged Ir–Ni complexes and its applications in organic coupling reactions
The novel unimolecular Ir-Ni bimetallic system with the conjugated bridging ligand has been developed. Photoinduced cross-coupling reactions (C–O, C–S, C–N) demonstrated the enormous potential of a conjugately bridged Ir–Ni catalytic system.
Org. Chem. Front., 2022,9, 1797-1807
https://doi.org/10.1039/D1QO01817E
Synthesis of chiral pyridine-oxazolines via a catalytic asymmetric Heine reaction of meso-N-(2-picolinoyl)-aziridines
A series of novel chiral pyridine-oxazolines were synthesized via catalytic asymmetric Heine reaction of meso-N-(2-picolinoyl)-aziridines.
Org. Chem. Front., 2022,9, 1531-1535
https://doi.org/10.1039/D1QO01900G
Chiral phosphoric acid-catalyzed regio- and enantioselective reactions of functionalized propargylic alcohols
Chiral phosphoric acid has been utilized for covalent activation of propargylic alcohols to act as pre-catalyst. With this activation mode, a range of highly regio- and enantioenriched heterocyclic products could be generated efficiently from racemic propargylic alcohols.
Org. Chem. Front., 2022,9, 1234-1240
https://doi.org/10.1039/D1QO01864G
S-triggered Schmidt-type rearrangement of vinyl azides to access N-aryl-(trifluoromethylsulfinyl)acetamides
A novel S-induced Schmidt-type rearrangement of vinyl azides with CF3SO2Na is developed for synthesis of N-arylated 2-(trifluoromethylsulfinyl)acetamieds, which is mediated by triphosgene (BTC) under mild reaction conditions.
Org. Chem. Front., 2022,9, 1241-1246
https://doi.org/10.1039/D1QO01516H
Organocatalytic atroposelective construction of axially chiral nonsymmetric biaryltriols and their applications in asymmetric synthesis and heavy metal ion detection
Organocatalytic atroposelective construction of axially chiral nonsymmetric biaryltriols and their applications in asymmetric synthesis and heavy metal ion detection.
Org. Chem. Front., 2022,9, 923-928
https://doi.org/10.1039/D1QO01821C
An iron-catalyzed multicomponent reaction of cycloketone oxime esters, alkenes, DABCO·(SO2)2 and trimethylsilyl azide
The synthesis of β-azidosulfones starting from alkenes, cycloketone oxime esters, trimethylsilyl azide and a sulfur dioxide surrogate of DABCO·(SO2)2 under iron catalysis is developed.
Org. Chem. Front., 2022,9, 917-922
https://doi.org/10.1039/D1QO01842F
About this collection
Read our on-going collection of the hottest research published as advanced article from Organic Chemistry Frontiers in 2022. These articles are recommended by reviewers as being of significant novelty and interest. Congratulations to all the authors whose articles are featured!