Multi-catalyst promoted asymmetric relay reactions
In this highlight, cooperative multi-catalyst systems, especially bismetallic- and organo-catalyst mediated asymmetric relay reactions, are presented.
Selective modification of natural nucleophilic residues in peptides and proteins using arylpalladium complexes
The present review outlines the recent methodologies for selective arylation of natural nucleophilic residues within unprotected peptides and proteins promoted by arylpalladium complexes, which demonstrate the advantages and potential of organometallic palladium complexes in bioconjugation.
Selective carbonylation of benzene to benzaldehyde using a phosphorus–nitrogen PN3P–rhodium(I) complex
A PN3P–Rh(I) complex realizes the selective carbonylation of benzene to benzaldehyde without irradiation.
Influence of sulfonyl substituents on the decomposition of N-sulfonylhydrazones at room temperature
A systematic investigation on the influence of sulfonyl substituents on the decomposition of N-sulfonylhydrazones at room temperature is described.
Visible-light-mediated α-phosphorylation of N-aryl tertiary amines through the formation of electron-donor–acceptor complexes: synthetic and mechanistic studies
A visible light-mediated photocatalyst-free approach for the oxidative α-CH functionalization of N-aryl tertiary amines with secondary phosphine oxides has been developed.
Construction and heterogeneous photooxidization reactivity of a cyclodextrin/porphyrin polyrotaxane network
A supramolecular polyrotaxane network, based on a CD-based inclusion complex and porphyrin derivative, was synthesized by imine condensation reactions. Then it could be applied as a heterogeneous catalyst for generating singlet oxygen under photoirradiation, which showed its good ability to photooxidize anthracene derivatives.
Biomimetic syntheses of C23 terpenoids: structural revision of salyunnanin A and confirmation of hassanane
Salyunnanin A and hassanane, two C23 terpenoids, were achieved from (+)-carnosic acid in 6 and 5 steps, respectively.
Photoinduced synthesis of (E)-vinyl sulfones through the insertion of sulfur dioxide
Under visible light irradiation, a three-component reaction of potassium alkyltrifluoroborates, sulfur dioxide and alkynes with the assistance of photocatalysis and in the presence of copper(II) triflate is described. This transformation affords (E)-vinyl sulfones efficiently with excellent regioselectivity and stereoselectivity under mild conditions.
Electrochemical synthesis of 7-membered carbocycles through cascade 5-exo-trig/7-endo-trig radical cyclization
An electrochemical synthesis of functionalized 7-membered carbocycles through a 5-exo-trig/7-endo-trig radical cyclization cascade has been developed.
Palladium-catalyzed asymmetric annulation between aryl iodides and racemic epoxides using a chiral norbornene cocatalyst
The first chiral norbornene scaffold-promoted asymmetric Catellani-type reaction using aryl iodides is reported.
DDQ-mediated regioselective C–S bond formation: efficient access to allylic sulfides
A novel metal-free dehydrocoupling approach for constructing allylic sulfides via oxidative allylic C–H functionalization with high atom- and step-economy has been developed.
Dual photoredox and nickel-catalyzed desymmetric C–O coupling reactions: visible light-mediated enantioselective synthesis of 1,4-benzodioxanes
Chiral 2,2′-bipyridine ligands are key to success in an enantioselective desymmetric C–O cross coupling reaction via dual visible light photoredox and nickel catalysis, resulting in chiral 1,4-benzodioxanes under mild reaction conditions.
Enantioselective access to multi-cyclic α-amino phosphonates via carbene-catalyzed cycloaddition reactions between enals and six-membered cyclic imines
A carbene-catalyzed enantioselective [4 + 2] cycloaddition reaction is developed and quarternary α-amino phosphonates are afforded with encouraging anti-bacterial activities.
Iridium-catalyzed oxidative Ar–H/Ar–H cross-coupling of primary benzamides with thiophenes
Described herein is an iridium(III)-catalyzed oxidative Ar–H/Ar–H cross-coupling of primary benzamides with thiophenes for the synthesis of (2-thienyl)benzamides.
Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines
Metal free 1,3-dipolar cycloaddition between alkenylazaarenes and nitrones has been developed for the synthesis of 4-substituted isoxazolidines and 5-substituted isoxazolidines in good yields and selectivities.
Palladium-catalyzed denitrogenative cycloadditions and alkenylations of benzotriazoles with alkynes
Palladium-catalyzed denitrogenative cycloadditions and alkenylations of benzotriazoles with alkynes have been achieved under different conditions, which enable the divergent syntheses of three types of valuable scaffolds.
Conductive fullerene surfactants via anion doping as cathode interlayers for efficient organic and perovskite solar cells
Conductive fullerenes, with mild solution-processing capabilities, are developed as electron transporting materials for efficient organic and perovskite solar cells.
Dearomatization of naphthols using oxy-allyl cations: efficient construction of α-all-carbon quaternary center-containing 2-(2-oxocycloalkyl)cycloalkyl diketones
An efficient strategy for the dearomatization of both α- and β-naphthols using in situ generated oxy-allyl cations is reported.
Hydrofunctionalization of alkenols triggered by the addition of diverse radicals to unactivated alkenes and subsequent remote hydrogen atom translocation
Concomitant anti-Markovnikov hydrofunctionalization of alkenes and oxidation of remote alcohols are achieved through intramolecular 1,5(6)-hydrogen atom transfer.
Optically active N-alkyl aziridines via stereospecific reductive cyclization of α-mesylated acetamides
An efficient method for the synthesis of optically active N-alkyl aziridines has been realized for the first time by stereospecific reductive cyclization of optically active α-mesylated acetamides. A series of optically active N-alkyl aziridines are prepared in moderate to good yields and excellent ees.
Photoinduced fragmentation-rearrangement sequence of cycloketoxime esters
A novel rearrangement of cycloketoxime esters to cyano-containing benzoates beyond the traditional Beckmann and Neber rearrangement process has been established in the presence of photocatalysis catalysis.
Differential calixarene receptors create patterns that discriminate glycosaminoglycans
A well-designed fluorescence displacement sensing array based on calixarene receptors realizes the discrimination of glycosaminoglycans.
Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation
A new type of 2,4-dienal featuring a benzofulvene skeleton is utilised in asymmetric Diels–Alder cycloadditions with 3-olefinic oxindoles via trienamine catalysis.
Bromide-catalyzed electrochemical trifluoromethylation/cyclization of N-arylacrylamides with low catalyst loading
An electro-generated trifluoromethyl radical mediated by a bromide ion is efficiently applied to the trifluoromethylarylation/cyclization of N-arylacrylamides.
Total synthesis of (±)-swermirin
The synthesis of swermirin features two sequential regioselective Stille couplings and a spontaneous 6π-electrocyclization.
Cu(I)-Catalyzed stereoselective synthesis of trisubstituted Z-enol esters via interrupting the 1,3-O-transposition reaction
An efficient Cu(I)-catalyzed stereoselective synthesis of trisubstituted Z-enol esters via interrupting the 1,3-O-transposition process is reported, which provided a convenient approach to highly functionalized Z-enol esters.
Copper-catalyzed oxidative functionalization of benzylic C–H bonds with quinazoline 3-oxides
A highly efficient copper-catalyzed oxidative functionalization of benzylic C(sp3)–H bonds with quinazoline 3-oxides has been developed.
Gold-catalyzed cascade cyclization of N-propargyl ynamides: rapid access to functionalized indeno[1,2-c]pyrroles
A new gold-catalyzed cascade cyclization of N-propargyl ynamides involving a presumable vinyl cation intermediate has been developed, allowing the efficient and practical synthesis of various functionalized indeno[1,2-c]pyrroles.
Pd(II)-Catalyzed [3 + 2] spiroannulation of α-aryl-β-naphthols with alkynes via a C–H activation/dearomatization approach
A Pd(II)-catalyzed [3 + 2] spiroannulation of α-aryl-β-naphthols with internal alkynes has been developed by relying on a C–H activation/arene dearomatization approach.
Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide under photocatalysis
Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide promoted by visible light is developed, leading to sulfonated tetrahydrofurans and related compounds in moderate to good yields.
Green carbon disulfide surrogate via a combination of potassium sulfide and chloroform for benzothiazine-thione and benzothiazole-thione construction
An efficient and green carbon disulfide surrogate via facile combination of potassium sulfide and chloroform has been developed.
Palladium-catalyzed reductive electrocarboxylation of allyl esters with carbon dioxide
Palladium-catalyzed regioselective electrocarboxylation of homostyrenyl acetates with CO2 has been successfully developed, providing α-aryl carboxylic acids with good selectivity and yield.
Sulfur mediated propargylic C–H alkylation of alkynes
Sulfur mediated propargylic C–H alkylation was realized through a one-pot procedure with modest yields and substrate scope. Hopefully, the community could find a better solution to this challenge by some novel metal-catalyzed reactions.
Pd-catalyzed carbonylation of aryl C–H bonds in benzamides with CO2
Herein, we report the first Pd-catalyzed carbonylation of unactivated aryl C–H bonds in benzamides under 1 atm of CO2 to directly afford important phthalimides.
Barium cation-responsive supra-amphiphile constructed by a new twisted cucurbituril/paraquat recognition motif in water
A new, strong, and barium cation-responsive host–guest recognition motif based on twisted cucurbituril and paraquat was established in water.
Selective formation of phthalimides from amines, aldehydes and CO by Pd-catalyzed oxidative C–H aminocarbonylation
The Pd/Cu-catalyzed intramolecular C–H bond aminocarbonylation utilizing imines as the amine source has been developed. This transformation provides an efficient and straightforward protocol for the synthesis of phthalimides which widely exist in natural products, pharmaceutical and functional materials. Various functional groups are tolerated and the yields are up to 99%.
Azidoheteroarylation of unactivated olefins through distal heteroaryl migration
A novel azidoheteroarylation of unactivated olefins by means of intramolecular distal heteroaryl migration is herein reported.
About this collection
Organic Chemistry Frontiers is delighted to present this collection of articles dedicated to Professor Lu Xiyan 陆熙炎 of Shanghai Institute of Organic Chemistry, celebrating his 90th birthday.
As a pioneer scientist in organometallics research, Professor Lu has made tremendous contribution for the development of organometallic chemistry directed towards organic synthesis and organocatalysis in China. His academic achievements have been widely recognised by the global chemistry community and inspired many latecomers to pursue research in the field.
Guest edited by Aiwen Lei (Wuhan University), this online collection highlights some of the most recent efforts in organometallics, catalysis, synthetic methodology development and other related areas within the broad organic chemistry.
More articles will be added as soon as they are published.