Recent trends and applications of the Cadiot–Chodkiewicz reaction
The Cadiot–Chodkiewicz reaction offers an elegant strategy for the formation of 1,3-diynes via Cu-catalyzed cross-coupling of alkynyl halides with terminal alkynes in the presence of an amine.
Application of copper(I) salt and fluoride promoted Stille coupling reactions in the synthesis of bioactive molecules
This review summarises the synthesis of bioactive molecules through the use of Cu(I) salt and fluoride promoted Stille coupling reactions.
Catalytic allylic functionalization via π-allyl palladium chemistry
This review highlights the palladium-catalyzed allylic C–H functionalizations via π-allyl palladium reported from early 2014 to present date.
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.
α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles
This review presents the use of α-alkyl- and α-alkoxy-halogenoacetamides as powerful partners for domino and 1,3-dipolar cycloaddition reactions resulting in a ring closure.
Modifications of amino acids using arenediazonium salts
Aryl transfer reactions from arenediazonium salts have started to make their impact in chemical biology with initial forays in the arena of arylative modifications and bio-conjugations of amino acids, peptides and proteins.
Hypervalent iodine reactions utilized in carbon–carbon bond formations
This review covers recent developments of hypervalent iodine chemistry in dearomatizations, radicals, hypervalent iodine-guided electrophilic substitution, arylations, photoredox, and more.
Consecutive multicomponent reactions for the synthesis of complex molecules
Consecutive multicomponent reactions (MCRs) combine two or more MCRs to achieve high synthetic efficiency, product structural diversity, and molecular complexity.
Recent advances in the synthesis of oxaspirolactones and their application in the total synthesis of related natural products
Oxaspirolactones are ubiquitous structural motifs found in natural products and synthetic molecules with a diverse biochemical and physicochemical profile, and represent a valuable target in natural product chemistry and medicinal chemistry.
Recent advances in catalytic asymmetric intermolecular oxidation of alkynes
In recent years, gold-metal-catalyzed intermolecular alkyne oxidation by an N-oxide oxidant, which presumably involves a gold carbenoid intermediate, has attracted increasing attention because it circumvents the employment of hazardous and potentially explosive diazocarbonyl compounds as starting materials for carbene generation.
Traceless point-to-axial chirality exchange in the atropselective synthesis of biaryls/heterobiaryls
A strategy for establishing a chiral axis from stereogenic centers via elimination or oxidative aromatization with a high level of chirality transfer was developed.
Hantzsch esters: an emerging versatile class of reagents in photoredox catalyzed organic synthesis
This minireview highlights the recent advances in the chemistry of Hantzsch esters in photoredox catalyzed organic synthesis, with particular emphasis placed on reaction mechanisms.
Recent advances and applications of p-toluenesulfonylmethyl isocyanide (TosMIC)
TosMIC, a unique and multifunctional synthetic reagent, reacts with a wide spectrum of synthons to deliver novel scaffolds.
Late stage functionalization of heterocycles using hypervalent iodine(III) reagents
Iodine(III) reagents represent a powerful tool for the late-stage functionalization of a variety of heterocycles through a range of transformations.
Organoboron synthesis via ring opening coupling reactions
This review covers new trends towards the selective synthesis of organoboron compounds where boron reagents and cyclic substrates participate in the generation of carbanions, in the presence of stoichiometric amounts of main-group metals or catalytic amounts of transition metal complexes, via ring opening coupling transformations.
Recent advances in the borylative transformation of carbonyl and carboxyl compounds
The recent advances in the borylative transformation of carbonyl and carboxyl compounds are summarized.
Recent advances in the direct functionalization of quinoxalin-2(1H)-ones
The direct C3-functionalization of quinoxalin-2(1H)-ones via C–H bond activation has recently attracted considerable attention, due to their diverse biological activities and chemical properties.
The Lossen rearrangement from free hydroxamic acids
During more than a century, the Lossen rearrangement was supposed to occur exclusively in the presence of stochiometric amount of activating reagents. Very recently, it was demonstrated that the Lossen rearrangement can take place directly from free hydroxamic acids offering a renewal of interest for this reaction.
Employment of α-nitroketones in organic synthesis
This review summarizes the recent developments of the reactions of α-nitroketones and the consequent formation of a variety of structural frameworks is discussed.
Chloroform as a CO surrogate: applications and recent developments
Transition-metal-catalyzed carbonylation reaction using chloroform as CO surrogate to synthesize carbonylated heterocyclic moieties.
Synthetic strategies for fluorination of carbohydrates
Different synthetic strategies for accomplishing regio- and stereoselective fluorinations of carbohydrate scaffolds are discussed in light of the biological implications arising from such substitutions.
Photochemical C–H bond coupling for (hetero)aryl C(sp2)–C(sp3) bond construction
This review highlights the recent advances in photochemical (hetero)aryl C(sp2)–C(sp3) bond construction via C–H bond coupling such as (hetero)arylation of C(sp3)–H bonds and alkylation of (hetero)aryl C(sp2)–H bonds.
Allylic azides: synthesis, reactivity, and the Winstein rearrangement
Allylic azides are useful synthetic intermediates, the Winstein rearrangement complicates usage, and mechanistic knowledge can enable selectivity.
Recent advances in the asymmetric synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-Michael reactions
In this review, recent applications of a stereoselective aza-Michael reaction for asymmetric synthesis of naturally occurring N-containing heterocyclic scaffolds and their usefulness to pharmacology are summarized.
Catalytic enantioselective iodolactonization reactions
The recent advances of catalytic enantioselective iodolactonizations of γ- or δ-substituted alkenoic carboxylic acids have been reviewed. The different catalysts and substrates are highlighted.
Recent advances in metal-free aerobic C–H activation
An overview of recent reactions based on the metal-free, dioxygen-induced, C–H activation of various radical precursors.
Recent advances in the synthesis of C2-spiropseudoindoxyls
This review summarizes the recent development of novel approaches to construct structurally unique oxindoles featuring a spirocycle at the C2 position.
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.
Use of ArSO2SRf reagents: an efficient tool for the introduction of SRf moieties
This review discusses the use of several ArSO2SRf reagents as SRf sources, an emerging trend to access SRf-containing molecules.
Intermolecular alkene difunctionalizations for the synthesis of saturated heterocycles
Intermolecular alkene difunctionalizations for the direct synthesis of saturated heterocycles.
Next generation diversity-oriented synthesis: a paradigm shift from chemical diversity to biological diversity
Diversity-oriented synthesis adds biological performance as a new diversity element.
Recent advances in homogeneous borrowing hydrogen catalysis using earth-abundant first row transition metals
The review highlights the recent advances (2013-present) in the use of earth-abundant first row transition metals in homogeneous borrowing hydrogen catalysis.
Applications of N′-monofunctionalised TsDPEN derivatives in asymmetric catalysis
N′-Monoalkylated or N′-mono(thio)acylated(N-sulfonyl)-1,2-diphenylethylene-1,2-diamine (TsDPEN) derivatives are have found extensive applications in asymmetric catalysis of a wide range of synthetic applications.
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.
SuperQuat chiral auxiliaries: design, synthesis, and utility
The design, synthesis and outline of some of the most common synthetic applications of the SuperQuat (4-substituted 5,5-dimethyloxazolidine-2-one) family of chiral auxiliaries, developed to address the shortcomings of the Evans (4-substituted oxazolidin-2-one) family of chiral auxiliaries, are presented.
Chemistry of detrifluoroacetylatively in situ generated fluoro-enolates
This review article provides a summary of the detrifluoroacetylative in situ generation of fluorine-containing enolates and their related reactions.
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.
Cascade reaction based synthetic strategies targeting biologically intriguing indole polycycles
In this review, cascade reaction based synthesis strategies delivering biologically intriguing indole polycycles are presented.
Non-toxic cyanide sources and cyanating agents
This review focuses on alternative cyanide sources and cyanating agents which are less hazardous than HCN or its salts.
Recent methods for the synthesis of α-acyloxy ketones
The present review provides a broad description of the methods reported for the synthesis of α-acyloxy ketones and some of their derivatives.
Synthetic manipulations of polyunsaturated fatty acids as a convenient strategy for the synthesis of bioactive compounds
The utilization of commercial polyunsaturated fatty acids in semi-syntheses of polyunsaturated natural products and derivatives has been reviewed.
Multicomponent reactions: a sustainable tool to 1,2- and 1,3-azoles
The present review outlines the recent advancements and pioneering efforts on the synthesis of 1,2/1,3-azoles employing a multicomponent strategy.
Donor- and acceptor-enynals/enynones
Three kinds of transformations based on benzo-fused donor- and acceptor-enynals/enynones, including reactions with alkenes, alkynes, and H2O, were discussed.
Catalytic carbene/alkyne metathesis (CAM): a versatile strategy for alkyne bifunctionalization
Cascade reactions involving a catalytic carbene/alkyne metathesis (CAM) process through a vinyl carbene intermediate provide an efficient and step-economic approach for the construction of polycyclic frameworks with structural diversity.
Catalytic dehydrogenative aromatization of cyclohexanones and cyclohexenones
Prompted by the scant attention paid by published literature reviews to the comprehensive catalytic dehydrogenative aromatization of cyclohexa(e)nones, this review describes recent methods developed to-date involving transition-metal-catalyzed oxidative aromatization and metal-free strategies for the transformation of cyclohexa(e)nones to substituted phenols.
Decarbonylative cross-coupling of amides
We present recent advances and key developments in the field of decarbonylative cross-coupling reactions of amides by a formal double N–C/C–C bond activation as well as discuss future challenges and potential applications for this exciting field.
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.
Recent progress in the synthesis of phosphorus-containing indole derivatives
Phosphorus-containing indole derivatives represent a special class of phosphorus-containing nitrogen heterocycles. This review summarizes the recent progress in the synthesis of such compounds, briefly discusses the reaction mechanisms and challenges, and outlines the synthetic opportunities still open.
Cyclic imines – preparation and application in synthesis
Cyclic imines, available from various nitrogen-containing reactants, serve as versatile synthetic intermediates for biologically active compounds.
Recent advances in the synthesis of cyclopropanes
Cyclopropanes have gained much attention by virtue of their interesting structure and unique reactivity. This review discusses the recent advances in the synthesis of cyclopropanes, and some of the related applications will be discussed.
Recent developments and applications of cyanamides in electrophilic cyanation
This review summarizes the recent developments and applications of readily accessible cyanamides in the electrophilic cyanation of various nucleophiles.
Recent developments in functionalization of acyclic α-keto amides
This review describes the synthetic utility of α-keto amides to synthesize various important molecules via mono, dual and triple functionalization reactions.
Recent advances in β-lactam synthesis
During the past century, β-lactams have been identified as the core of penicillin and since then several strategies have been developed for their synthesis.
C–H alkylation reactions of indoles mediated by Pd(II) and norbornene: applications and recent developments
Recent synthetic applications and methodological advancements of the Pd(II)-catalyzed C2 functionalisation of indoles are highlighted and discussed in this review.
Recent advances in the annulation of Morita–Baylis–Hillman adducts
In this review, we summarize some of the most recent advances in the construction of cyclic compounds from the annulation of Morita–Baylis–Hillman (MBH) adducts, which have demonstrated their importance by possessing diverse functional groups.
Photoorganocatalysis, small organic molecules and light in the service of organic synthesis: the awakening of a sleeping giant
This review is focused on recent developments in the use of small organic molecules as photocatalysts.
Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C–H bonds in a single operation
This review describes recent developments in the use of catalytic transient directing groups, through imine linkages, which in combination with transition metal catalysts provide streamlined C–H functionalisation processes.
Copper nitrate: a privileged reagent for organic synthesis
This review demonstrates the state-of-the-art applications of copper nitrate as a nitration reagent, oxidant, catalyst, promoter and precursor of nitrile oxides.
Synthesis of polyheterocycles via multicomponent reactions
Polyheterocycles are one of the most desired synthetic targets due to their numerous and valuable applications in various fields.
C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process
This review is focused on the recent advances in the C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process. Diverse substituted hydrazones including N-heterocycles are afforded under mild conditions with excellent selectivities. In general, an aminyl radical as the key intermediate is involved during the reaction process.
Nitrilium ions – synthesis and applications
Access to both stable and transient nitrilium ions and the use of these synthons in the organic synthesis of imines and a large spectrum of heterocycles and transition metal complexes are succinctly summarized.
Iodine-catalyzed guanylation of amines with N,N′-di-Boc-thiourea
Iodine-catalyzed guanylation of amines with N,N′-di-Boc-thiourea is especially useful for both electronically and sterically deactivated primary anilines.
Rh-Catalyzed domino synthesis of 4-hydroxy-3-methylcoumarins via branch-selective hydroacylation
A Rh-catalyzed domino synthesis of 4-hydroxy-3-methylcoumarins via branch-selective hydroacylation of acrylates and acrylamides using salicylaldehydes is described.
Solvent- and catalyst-free transamidation reaction of unprotected glycosyl carboxamides.
Functionalization of activated methylene C–H bonds with nitroarenes and sulfur for the synthesis of thioamides
Synthesis of arylthioamides from nitroarenes is reported for the first time. Phenylacetic acids or benzyl alcohols could be used as benzyl synthons.
A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution
A microwave assisted multicomponent protocol on water allows the regioselective synthesis of chiral aryl-1,2-mercaptoamines. The enzymatic resolution of the racemates leads to enantioenriched products.
Hypervalent iodane mediated reactions of N-acetyl enamines for the synthesis of oxazoles and imidazoles
A hypervalent iodane reagent used for the intramolecular cyclization of N-acetyl enamines and intermolecular cyclocondensation of enamines and nitriles was investigated.
Construction of indazolo[3,2-a]isoquinolines via [3 + 2] cycloaddition of benzynes
A [3 + 2] annulation protocol for the construction of N-substituted indazolo[3,2-a]isoquinolines starting from benzynes and C,N-cyclic azomethine imines was developed. A diverse range of indazolo[3,2-a]isoquinolines can be easily accessed, which show good anti-proliferative activity on cancer cells.
Intermolecular Scandium Triflate-Promoted Nitrene-Transfer [5+1] Cycloadditions of Vinylcyclopropanes
Expeditious diastereoselective synthesis of medium ring heterocycle-fused chromenes via tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition
The first examples of highly diastereoselective tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition are described for the synthesis of medium ring heterocycle-fused chromenes.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to synthetic methodology.