Advances in asymmetric visible-light photocatalysis, 2015–2019
Asymmetric visible-light photocatalysis has recently drawn considerable attention of the scientific community owing to its unique activation modes and significance for the enantioselective green synthesis.
Hetero-bimetallic cooperative catalysis for the synthesis of heteroarenes
Review covering the synthesis of 5- and 6-membered as well as condensed heteroarenes, focussing on the combinations in cooperative catalytic systems in strategies used to achieve selectivity and also highlights the mode of action for the cooperative catalysis leading to the synthesis of commercially and biologically relevant heteroarenes.
Combining enzymes and organometallic complexes: novel artificial metalloenzymes and hybrid systems for C–H activation chemistry
This review describes the advances in the design and application of novel artificial metalloenzymes in C–H activation reactions.
Reversal of enantioselectivity in chiral metal complex-catalyzed asymmetric reactions
The achievements of chiral metal complex-catalyzed enantiodivergent reactions during the period from 2008 to present were updated.
Introduction to chemical warfare agents, relevant simulants and modern neutralisation methods
This short review presents the current main chemical warfare agents and their most relevant simulants, and the recent catalytic and selective methods for their soft neutralization, potentially usable in the future as an alternative to “heavy” methods for decontamination.
Chiral palladium pincer complexes for asymmetric catalytic reactions
This review covers the methods for the preparation of chiral palladium(II) pincer complexes and their applications in asymmetric catalysis.
Metal-catalysed reactions enabled by guanidine-type ligands
A review of metal–guanidine complexes, which are selective and powerful catalysts for organic transformations, asymmetric synthesis, and polymerisation.
Recent advances in photocatalytic manipulations of Rose Bengal in organic synthesis
This review highlights the recent advances in photocatalytic manipulations of Rose Bengal in organic synthesis.
Catalytic asymmetric cycloaddition reactions of enoldiazo compounds
Review of recent advances in asymmetric catalytic cycloaddition reactions of silyl-protected enoldiazo compounds.
The mechanistic duality of (thio)urea organocatalysts for ring-opening polymerization
Dual mechanisms for H-bond mediated ring-opening polymerization allow for precise control, high activity and new applications.
The roles of Lewis acidic additives in organotransition metal catalysis
We present recent advances in prominent organotransition metal-catalysed reactions in which Lewis acid cocatalysts are employed to increase catalyst activity or selectivity. The roles of Lewis acids are discussed.
N-Alkyl amide synthesis via N-alkylation of amides with alcohols
The present review summarizes the recent development of N-alkylation of amides with alcohols according to the classification of catalysts.
Beyond the traditional roles of Ag in catalysis: the transmetalating ability of organosilver(I) species in Pd-catalysed reactions
The role of silver salts in Pd-catalysed C–C bond forming transformations.
The challenge of using isopropylamine as an amine donor in transaminase catalysed reactions
Factors that affect the efficiency of amine transaminase catalyzed reactions using isopropylamine as an amine donor.
Recent advances in transition metal-catalyzed C(sp2)–H nitration
This review updates advances of direct C(sp2)–H nitration for the synthesis of nitroaromatic compounds and the mechanisms during the past decade.
Recent developments in photochemical reactions of diazo compounds
Chemistry of diazo compounds is dominated by transition metal catalysis but recently, photoinitiated reactions of diazo compounds have attracted a lot of attention. This mini-review describes recent discoveries on the reactivity of diazo compounds under light irradiation.
The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art
This Review article provides a summary and critical metrics-based analysis of recently developed catalytic Mitsunobu reactions.
Indium(III) as π-acid catalyst for the electrophilic activation of carbon–carbon unsaturated systems
This review focuses on indium(III) as a π-acid for the activation of C–C unsaturated systems (alkynes, alkenes, and allenes) in organic synthesis.
Dibenzofuran-4,6-bis(oxazoline) (DBFOX). A novel trans-chelating bis(oxazoline) ligand for asymmetric reactions
The trans-chelating bis(oxazoline) ligand (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) [(R,R)-DBFOX/Ph] coordinates metal ions to give C2-symmetric complexes which effectively catalyze a variety of asymmetric reactions.
Asymmetric iodine catalysis-mediated enantioselective oxidative transformations
The implementation of chiral iodine catalysis has tremendously been developed in the field of asymmetric synthesis over the past decade.
Development and application of chiral spirocyclic phosphoric acids in asymmetric catalysis
This review describes the synthetic methods for the preparation of chiral spirocyclic phosphoric acids (SPAs), and their dynamically developing application for catalytic enantioselective transformations.
Halo-substituted benzenesulfonyls and benzenesulfinates: convenient sources of arenes in metal-catalyzed C–C bond formation reactions for the straightforward access to halo-substituted arenes
The use of halo-substituted ArSO2R as an aryl source in metal-catalyzed C–C bond formation reactions presents several advantages, as the reaction often proceeds without cleavage of the C–halo bonds.
Chiral proton-transfer shuttle catalysts for carbene insertion reactions
The development of chiral proton-transfer shuttles provides a totally new enantiocontrol strategy for transition metal-catalyzed asymmetric carbene insertion reactions.
Recent advances in iodine mediated electrochemical oxidative cross-coupling
This review article gives an overview of the recent development of iodine mediated electrochemical oxidative coupling reactions.
Catalytic asymmetric enamine protonation reaction
Recent advances in catalytic enantioselective enamine protonation for the synthesis of optically active carbonyl compounds are summarized in this review.
Enhanced structural diversity in terpenoid biosynthesis: enzymes, substrates and cofactors
Terpenoid structural diversity is enhanced by multiproduct enzymes. Biosynthesis can be altered by switch in substrates, cofactors and pH.
Cercosporin-photocatalyzed sp3 (C–H) activation for the synthesis of pyrrolo[3,4-c]quinolones
A metal-free cercosporin-photocatalyzed sp3 (C–H) activation for the synthesis of pyrrolo[3,4-c]quinolones was developed under mild conditions.
Palladium(II) ligated with a selenated (Se, CNHC, N−)-type pincer ligand: an efficient catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling in water
First Pd(II) complex of a novel (Se, CNHC, N−) type pincer ligand based on selenated NHC was synthesized and found to be very efficient in the catalysis of Mizoroki–Heck coupling of ArCl/Br and Suzuki–Miyaura coupling of ArBr in water.
Tailoring chemoenzymatic oxidation via in situ peracids
P-Chiral, N-phosphoryl sulfonamide Brønsted acids with an intramolecular hydrogen bond interaction that modulates organocatalysis
An intramolecular H-bond in the Brønsted acid OttoPhosa I accelerates the reaction and increases enantioselectivity for the transfer hydrogenation of quinolines.
Three-component difluoroalkylamination of alkenes mediated by photoredox and iron cooperative catalysis
A new three-component difluoroalkylamination of alkenes mediated by photoredox and iron cooperative catalysis has been developed with a broad substrate scope.
Silver-promoted decarboxylative radical addition/annulation of oxamic acids with gem-difluoroolefins: concise access to CF2-containing 3,4-dihydroquinolin-2-ones
Described is a silver-promoted decarboxylative radical addition/annulation of oxamic acids with gem-difluoroalkenes enabling the convenient synthesis of various structurally diverse CF2-containing 3,4-dihydroquinolin-2-ones that might find applications in medical chemistry.
An asymmetric iminium ion catalysis-enabled cascade cycloaddition reaction of chromone-oxindole synthons with enals: construction of a spirooxindole–hexahydroxanthone framework
We report the first asymmetric iminium ion catalysis-enabled cascade cycloaddition reaction of bifunctional chromone-oxindole synthons and α,β-unsaturated aldehydes.
Enantioselective construction of 3-substituted 3-amino-2-oxindoles containing an N,N-ketal skeleton via organocatalyzed aza-addition of isatin imines
The first example of organocatalytic chemo-, regio- and enantioselective aza-Mannich reactions of triazoles and arylamines, respectively, with isatin-derived imines has been achieved.
Design and application of diimine-based copper(I) complexes in photoredox catalysis
Novel copper catalysts were designed, synthesized and utilized in visible light-driven photocatalytic ATRA reactions.
Organocatalytic asymmetric spirocyclization reactions of cyclic 2,4-dienones with cyanoketones: synthesis of spiro-dihydropyrano cyclohexanones
The first organocatalytic asymmetric synthesis of spiro-dihydropyrano cyclohexanones has been developed via the cascade reaction between cyanoketones and cyclic 2,4-dienones.
Iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide by the use of a borrowing hydrogen methodology
An iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide was developed under basic conditions, affording the optically active secondary sulfinamides in high yields and diastereoselectivities.
Highly enantioselective addition of sulfur-containing heterocycles to isatin-derived ketimines
In this study, we report a highly stereoselective addition of sulfur-containing heterocyclic compounds to isatin-derived ketimines efficiently catalyzed by cinchonidine-derived bifunctional tertiary aminothiourea (1 mol%).
Pyridine-catalyzed desulfonative borylation of benzyl sulfones
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B2pin2).
Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones
Increased reactivity of α-methylene-γ-butyrolactones towards tertiary phosphines is reported; this effect is used to improve the efficiency of phosphine-catalyzed reactions.
Visible-light photocatalytic aerobic oxidation of sulfides to sulfoxides with a perylene diimide photocatalyst
Under visible light, a metal-free aerobic selective sulfoxidation photosensitized by a perylene diimide photocatalyst has been developed.
Fe-Catalyzed enaminone synthesis from ketones and amines
A novel Fe-catalyzed β-functionalization of ketones with amines for constructing enaminones has been demonstrated.
Regio- and stereoselective [3 + 2] cycloaddition reaction: access to isoxazole-dispirobisoxindoles featuring three contiguous stereocenters
A novel methodology toward the diversity-oriented asymmetric construction of densely functionalized isoxazole-dispirobisoxindoles was developed.
Organocatalytic asymmetric synthesis of dihydrofuran-spirooxindoles from benzylidene malononitriles and dioxindoles
The first organocatalytic asymmetric synthesis of dihydrofuran-spirooxindoles having a linkage at the 2-position of the dihydrofuran motif has been developed from dioxindoles and benzylidene malononitriles.
One stone two birds: cobalt-catalyzed in situ generation of isocyanates and benzyl alcohols for the synthesis of N-aryl carbamates
An efficient method for the synthesis of N-aryl carbamates from N-Boc-protected amines has been developed.
Visible-light mediated sulfonylation of thiols via insertion of sulfur dioxide
Photocatalytically generated sulfenyl radicals were coupled with arylsulfonyl radicals at room temperature for accessing unsymmetrical organic thiosulfonates.
NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes
An air-stable N-heterocyclic carbene–copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan).
Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones
An efficient organocatalyzed asymmetric Henry reaction between α-fluoroketones and nitroalkanes has been developed.
Photocatalytic aerobic α-thiolation/annulation of carbonyls with mercaptobenzimidazoles
A concise aerobic photocatalysis using a blue LED combined with a Lewis acid has been developed to enable α-thiolation/annulation of carbonyls.
Deoxygenative cross-electrophile coupling of benzyl chloroformates with aryl iodides
We disclose herein a Ni-catalyzed benzyl C–O bond radical fragmentation/cross-electrophile coupling of benzyl chloroformates with aryl iodides to generate diaryl methane derivatives.
Visible light mediated oxidative lactonization of 2-methyl-1,1′-biaryls for the synthesis of benzocoumarins
A visible light mediated C–H lactonization of 2-methyl-1,1′-biaryls with oxygen as the oxidant was developed, giving benzocoumarins in good yields.
Radical fluoroalkylation reactions of (hetero)arenes and sulfides under red light photocatalysis
The use of Zn-phthalocyanine in a red-light-driven process for the perfluoroalkylation reactions of (hetero)arenes and sufides represents a friendlier environmental alternative.
Palladium-catalyzed allylic C–H oxidation under simple operation and mild conditions
We discovered an effective and simple system (Pd/BQ/air/r.t.) for making allylic alcohols through Pd-catalyzed allylic C–H bond functionalization.
Enantioselective synthesis of chiral heterocyclic biaryls via asymmetric Suzuki–Miyaura cross-coupling of 3-bromopyridine derivatives
A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki–Miyaura coupling.
Copper-catalyzed carbene/alkyne metathesis terminated with the Buchner reaction: synthesis of dihydrocyclohepta[b]indoles
A copper-catalyzed carbene/alkyne metathesis reaction of alkyne-tethered diazoacetates is reported, which provides dihydrocyclohepta[b]indole skeletons under mild reaction conditions.
Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids
Chiral multifunctional thiourea/boronic acid catalysts enabled the synthesis of N-hydroxyaspartate derivatives applicable for KAHA amidation through acid-β selective aza-Michael addition.
Iron catalysed selective reduction of esters to alcohols
Exposure of BIANFeCl2 to nBuLi generates an anionic complex which is a competent catalyst for the selective reduction of esters to alcohols.
Copper-catalyzed arene amination in pure aqueous ammonia
A simple protocol for copper-catalyzed arene amination using aqueous ammonia without any additional ligands and organic coordinating solvents has been developed.
Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes
A simple and efficient iron-catalyzed protodehalogenation of alkyl and aryl halides using phenylhydrosilane is disclosed.
Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes
Simple cationic bis(phosphine)iridium complexes are shown to be highly selective catalysts for ether cleavage with silanes. Benzylic ethers can be cleaved under mild conditions in the presence of reductively-labile functional groups.
Organocatalytic asymmetric Michael/hemiketalization/acyl transfer reaction of 1,3-propanediones with (E)-2-(2-nitrovinyl)phenols
An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between (E)-2-(2-nitrovinyl)phenols and 1,3-propanediones is disclosed to generate products having keto, ester and nitro functionalities.
Biochemical studies of a β-1,4-rhamnoslytransferase from Streptococcus pneumonia serotype 23F
A new β-rhamnoslytransferase Cps23FT from Streptococcus pneumonia serotype 23F was functionally explored for the first time.
Efficient synthesis of chiral β-hydroxy sulfones via iridium-catalyzed hydrogenation
A highly efficient Ir-catalyzed asymmetric hydrogenation of prochiral β-keto sulfones was successfully developed, affording a series of chiral β-hydroxy sulfones with excellent results (up to >99% conversion, 99% yield, >99% ee, and 20 000 TON).
Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes
The catalytic asymmetric synthesis of mono-fluoro-, -chloro- and -bromomethyl-1,2-diaryl ester cyclopropanes is described.
Conversion of aldimines to secondary amines using iron-catalysed hydrosilylation
Hydrosilylation of imines was achieved using a redox non-innocent Fe-BIAN catalyst and employing the inexpensive trialkoxysilane (EtO)3SiH.
Organocatalytic asymmetric synthesis of highly substituted pyrrolidines bearing a stereogenic quaternary centre at the 3-position
An organocatalytic asymmetric cascade reaction has been developed between N-tosyl aminomethyl enones and trans-α-cyano-α,β-unsaturated ketones for the synthesis of highly substituted pyrrolidines having a stereogenic quaternary centre at the 3-position.
Direct enantio- and diastereoselective Mannich reactions of isatin-derived ketimines with oxo-indanecarboxylates catalyzed by chiral thiourea derived from hydroquinidine
A series of 3-substituted 3-amino-oxindoles were constructed by this protocol in excellent yields (92–99%) with high enantioselectivities (85–99% ee) and diastereoselectivities (up to >99 : 1 dr).
Asymmetric synthesis of β-amino ketones by using cinchona alkaloid-based chiral phase transfer catalysts
A highly enantioselective nucleophilic addition of ketones to versatile imines catalyzed by chiral PTC has been developed, and the process affords the Mannich reaction products with tertiary stereocenters in good to high yields and excellent enantioselectivities. This protocol is effective for gram scale reaction.
Base-catalyzed selective esterification of alcohols with unactivated esters
tert-Butyl esters were identified as efficient esterification reagents for base-catalyzed esterification reactions, and mechanistic studies provided evidence of an exchange of the tert-butyl alkoxide metal with alcohol.
Direct synthesis of indenes via a rhodium-catalyzed multicomponent Csp2–H annulation reaction
A highly efficient, direct and multicomponent route for the synthesis of indenes is reported herein.
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The latest articles published in Organic and Biomolecular Chemistry related to catalysis and biocatalysis research.