Themed collection Synthetic methodology in OBC
Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review
Organocatalytic methods and light-mediated methods have proved to be effective in chemical synthetic science. This paper compares them with the more established metal-catalyzed methods for the synthesis of a pharmaceutical core: coumarin.
Org. Biomol. Chem., 2022,20, 4846-4883
https://doi.org/10.1039/D2OB00491G
Hyperbaric reactions in organic synthesis. Progress from 2006 to 2021
This account systematizes a hundred papers (2006–2021 yy) in order to highlight the advantages of hyperbaric conditions (1–20 kbar) in preparative organic synthesis.
Org. Biomol. Chem., 2022,20, 2320-2355
https://doi.org/10.1039/D1OB01423D
Recent developments in enantio- and diastereoselective hydrogenation of N-heteroaromatic compounds
This review details the current scope of catalytic systems for the diastereo- and enantioselective hydrogenation of various N-heterocycles, while highlighting their applications to drug discovery.
Org. Biomol. Chem., 2022,20, 1794-1827
https://doi.org/10.1039/D1OB02331D
Synthetic approaches to 1,2,4-triazolo[5,1-c][1,2,4]triazin-7-ones as basic heterocyclic structures of the antiviral drug Riamilovir (“Triazavirin®”) active against SARS-CoV-2 (COVID-19)
In this review article, the currently available synthetic approaches to 1,2,4-triazolo[5,1-c][1,2,4]triazin-7-ones have been discussed. This moiety is considered as a basic heterocyclic structure of the antiviral drug Riamilovir (“Triazavirin®”).
Org. Biomol. Chem., 2022,20, 1828-1837
https://doi.org/10.1039/D1OB02125G
Cyclobutane based “overbred intermediates” and their exploration in organic synthesis
The strategic exploration of four-member “overbred intermediates” (cyclobutane based) in the total synthesis of a complex carbocyclic target structure from 1968 to 2020 is outlined in this short review.
Org. Biomol. Chem., 2022,20, 1582-1622
https://doi.org/10.1039/D1OB02361F
Enantioselective catalytic Povarov reactions
Catalytic asymmetric Povarov reactions are reviewed, with emphasis on the use of chiral Lewis and Brønsted acids, H-bond forming catalysts and aminocatalysis. Enantioselective nitroso Povarov and interrupted Povarov reactions are also discussed.
Org. Biomol. Chem., 2022,20, 1550-1581
https://doi.org/10.1039/D1OB02270A
Construction of aziridine, azetidine, indole and quinoline-like heterocycles via Pd-mediated C–H activation/annulation strategies
N-Heterocycles can be found in natural products and drug molecules and are indispensable components in the area of organic synthesis, medicinal chemistry and materials science.
Org. Biomol. Chem., 2022,20, 1339-1359
https://doi.org/10.1039/D1OB02146J
Reactivity switch-over of 4-hydroxydithiocoumarins under various conditions and their application in organic synthesis
Synthetic utilities of 4-hydroxydithiocoumarin were explored for the construction of numerous new heterocycles involving its three different reactive sites.
Org. Biomol. Chem., 2022,20, 715-726
https://doi.org/10.1039/D1OB01357B
Synthesis of oxindoles bearing a stereogenic 3-fluorinated carbon center from 3-fluorooxindoles
The present review summarizes the advances in the synthesis of 3,3-disubstituted 3-fluorooxindole derivatives through the straightforward functionalization of 3-fluorooxindoles.
Org. Biomol. Chem., 2022,20, 538-552
https://doi.org/10.1039/D1OB01964C
Phosphorylation of arenes, heteroarenes, alkenes, carbonyls and imines by dehydrogenative cross-coupling of P(O)–H and P(R)–H
This review offers an ample opportunity to take a journey through recent advancements in C–P bond formation reactions, along with their mechanistic pathways.
Org. Biomol. Chem., 2022,20, 498-537
https://doi.org/10.1039/D1OB02003J
Recent advances in palladium-catalyzed C(sp3)/C(sp2)–H bond functionalizations: access to C-branched glycosides
This review summarises recent developments in palladium-catalyzed directed and nondirected C–H functionalization approaches to access C-branched aryl/alkenyl/alkyl glycosides with reaction characteristics and proposed mechanisms.
Org. Biomol. Chem., 2022,20, 264-281
https://doi.org/10.1039/D1OB02142G
Recent developments in the synthesis of nitrogen-containing heterocycles from β-aminovinyl esters/ketones as CC–N donors
The synthesis of nitrogen-containing heterocycles from β-aminovinyl esters(ketones) was reviewed according to the classification of the final heterocycle synthesis.
Org. Biomol. Chem., 2022,20, 282-295
https://doi.org/10.1039/D1OB01998H
Catalytic asymmetric synthesis of α-stereogenic carboxylic acids: recent advances
This review illustrates recent advances and further potential of catalytic asymmetric synthesis of α-stereogenic free carboxylic acids from racemic or prochiral precursors.
Org. Biomol. Chem., 2022,20, 37-54
https://doi.org/10.1039/D1OB02038B
Direct radical functionalization methods to access substituted adamantanes and diamondoids
Substituted adamantanes are important and versatile products that can be derived from direct C–H to C–C transformations via radical intermediates. In this review, a wide range of direct functionalization methods are summarized with a focus on mechanism and scope.
Org. Biomol. Chem., 2022,20, 10-36
https://doi.org/10.1039/D1OB01916C
Current applications of kinetic resolution in the asymmetric synthesis of substituted pyrrolidines
This review summarises ways to construct substituted pyrrolidines employing kinetic resolution strategies involving methods as diverse as transition metal catalysis and biocatalysis.
Org. Biomol. Chem., 2021,19, 10493-10515
https://doi.org/10.1039/D1OB01943K
Synthesis of 2H-chromenes: recent advances and perspectives
Functionalized 2H-chromenes are one type of important oxygen heterocycle, and have widespread applications in many areas. This review mainly focuses on the two recently established synthetic strategies towards such compounds.
Org. Biomol. Chem., 2021,19, 10530-10548
https://doi.org/10.1039/D1OB01906F
Transition metal catalysed direct construction of 2-pyridone scaffolds through C–H bond functionalizations
A summary of literature on transition metal catalysed construction of 2-pyridone scaffolds using a wide range of coupling partners via C–H bond functionalizations has been described.
Org. Biomol. Chem., 2021,19, 10516-10529
https://doi.org/10.1039/D1OB01856F
Recent advances in the synthesis of indolizine and its derivatives by radical cyclization/cross-coupling
The free-radical-induced syntheses of indolizines were reviewed by type of catalyst.
Org. Biomol. Chem., 2021,19, 10245-10258
https://doi.org/10.1039/D1OB01431E
Recent advances in Cu-catalyzed transformations of internal alkynes to alkenes and heterocycles
Numerous metal-catalyzed reactions involving internal alkynes and aimed towards synthetically and pharmacologically important alkenes and heterocycles have appeared in the literature.
Org. Biomol. Chem., 2021,19, 10259-10287
https://doi.org/10.1039/D1OB01709H
β-Keto acids in asymmetric metal catalysis and organocatalysis
β-Keto acids: ideal ketone surrogates for diverse asymmetric nucleophilic addition reactions via a decarboxylative process.
Org. Biomol. Chem., 2021,19, 10030-10046
https://doi.org/10.1039/D1OB01481A
Transition metal-catalyzed arylation of unstrained C–C single bonds
Carbon–carbon bond activation is one of the most challenging and important research areas in organic chemistry.
Org. Biomol. Chem., 2021,19, 9809-9828
https://doi.org/10.1039/D1OB01707A
Ring closing metathesis for the construction of carbazole and indole-fused natural products
In this perspective, ring-closing metathesis (RCM) based approaches for the synthesis of carbazole derivatives and other indole-fused heteroaromatic systems have been described.
Org. Biomol. Chem., 2021,19, 9797-9808
https://doi.org/10.1039/D1OB01471D
N-Triflylphosphoramides: highly acidic catalysts for asymmetric transformations
N-Triflylphosphoramides (NTPA), have become increasingly popular catalysts in the development of enantioselective transformations as they are stronger Brønsted acids than the corresponding phosphoric acids (PA).
Org. Biomol. Chem., 2021,19, 9565-9618
https://doi.org/10.1039/D1OB01708J
C 1-Symmetric diphosphorus ligands in metal-catalyzed asymmetric hydrogenation to prepare chiral compounds
This review examines the potential of C1-symmetric diphosphorus ligands in metal-catalyzed asymmetric hydrogenation of alkenes to produce pharmaceutical intermediates, bioactive molecules, drug molecules, agrochemicals, and fragrances.
Org. Biomol. Chem., 2021,19, 9095-9137
https://doi.org/10.1039/D1OB01207J
The construction of benzimidazo[2,1-a]isoquinolin-6(5H)-ones from N-methacryloyl-2-phenylbenzoimidazoles through radical strategies
We highlight significant progress in the synthesis of benzimidazo[2,1-a]isoquinolin-6(5H)-ones using C-, S-, P-, and Si-centered radicals, including the selection of the catalytic system, substrate scope, mechanistic understanding, and applications.
Org. Biomol. Chem., 2021,19, 8874-8885
https://doi.org/10.1039/D1OB01465J
Recent advances in decarbonylative annulation reactions
In recent years, decarbonylative annulation reactions have emerged as one of the most efficient routes to construct a variety of important carbocyclic and heterocyclic scaffolds.
Org. Biomol. Chem., 2021,19, 8853-8873
https://doi.org/10.1039/D1OB00891A
Arylcyclopropane yet in its infancy: the challenges and recent advances in its functionalization
Development of straightforward protocols for the functionalization of unactivated cyclopropanes is still challenging, the realization of which could bestow the scientific community with a recurring building block for modern organic transformations.
Org. Biomol. Chem., 2021,19, 8627-8645
https://doi.org/10.1039/D1OB01432C
Oxidative cross-coupling of thiols for S–X (X = S, N, O, P, and C) bond formation: mechanistic aspects
This review describes the oxidative cross-couplings of thiols forming various organosulfur compounds, focusing on critical intermediates such as sulfenyl halides, thiyl radicals, sulfenium cations, disulfides, and organo-transition metal intermediates.
Org. Biomol. Chem., 2021,19, 8656-8686
https://doi.org/10.1039/D1OB01368H
Application of combined cyanide sources in cyanation reactions
The cyanation reaction is a key transformation due to the wide-ranging applications of nitrile compounds in organic chemistry.
Org. Biomol. Chem., 2021,19, 8646-8655
https://doi.org/10.1039/D1OB01520F
Recent strategies used in the synthesis of saturated four-membered heterocycles
Recent advances in the synthesis of O-, N-, and S-atom containing saturated 4-membered heterocycles are presented based on their preparative similarities. These strategic approaches highlight both progress made and remaining synthetic opportunities.
Org. Biomol. Chem., 2021,19, 8425-8441
https://doi.org/10.1039/D1OB00988E
Recent advances in rhodium-catalyzed C(sp2)–H (hetero)arylation
Recent achievements in rhodium-catalyzed arylations through C(sp2)–H bond activation were summarized.
Org. Biomol. Chem., 2021,19, 8442-8465
https://doi.org/10.1039/D1OB01190A
C–H activation reactions of nitroarenes: current status and outlook
The current landscape of nitro group directed C–H activation reactions of (hetero)arenes is reviewed.
Org. Biomol. Chem., 2021,19, 8409-8424
https://doi.org/10.1039/D1OB01455B
Recent advances and future challenges in the synthesis of 2,4,6-triarylpyridines
The present review is focused on recent advances (2015–present) in the synthesis of 2,4,6-triarylpyridines (also known as Kröhnke pyridines).
Org. Biomol. Chem., 2021,19, 8184-8204
https://doi.org/10.1039/D1OB01310F
The C–H functionalization of N-alkoxycarbamoyl indoles by transition metal catalysis
Indole and its congeners are ubiquitous nitrogen containing organic scaffolds found in a plethora of natural products. This review aims to highlight the transition-metal catalyzed C–H functionalization of N-alkoxycarbamoyl indoles.
Org. Biomol. Chem., 2021,19, 7949-7969
https://doi.org/10.1039/D1OB01121A
Current developments in the synthesis of 4-chromanone-derived compounds
The chroman-4-one framework is a significant structural entity that belongs to the class of oxygen-containing heterocycles.
Org. Biomol. Chem., 2021,19, 7995-8008
https://doi.org/10.1039/D1OB01352A
Forgotten and forbidden chemical reactions revitalised through continuous flow technology
This short review highlights compelling case studies from the last five years showcasing how modern flow technology has impacted and advanced synthetic chemistry in academia and industry.
Org. Biomol. Chem., 2021,19, 7737-7753
https://doi.org/10.1039/D1OB01452H
An update on the progress of cycloaddition reactions of 3-methyleneindolinones in the past decade: versatile approaches to spirooxindoles
This review focuses on important cycloaddition reactions of 3-methyleneindolinones to afford 3,3′-spirocyclic oxindoles.
Org. Biomol. Chem., 2021,19, 7768-7791
https://doi.org/10.1039/D1OB01176F
Recent developments in catalytic cross-couplings with unsaturated carboxylates
This review summarises the recent advances in the field of transition metal-catalyzed C–O bond activation of readily accessible unsaturated carboxylates with organometallics until May 2021.
Org. Biomol. Chem., 2021,19, 7754-7767
https://doi.org/10.1039/D1OB00955A
Recent advances in the synthesis of pyrrolo[1,2-a]indoles and their derivatives
This review focuses on recent developments in the synthesis of pyrrolo[1,2-a]indole derivatives. The mechanism, factors affecting the yield and selectivity of the product, and application to the synthesis of bioactive molecules are explained.
Org. Biomol. Chem., 2021,19, 7544-7574
https://doi.org/10.1039/D1OB01103K
2-Thiazolines: an update on synthetic methods and catalysis
This review summarizes the recent developments in the synthesis and catalytic applications of 2-thiazoline ligands with literature coverage mainly extending from 2009 to 2021.
Org. Biomol. Chem., 2021,19, 7497-7517
https://doi.org/10.1039/D1OB01180D
Recent progress in the radical α-C(sp3)–H functionalization of ketones
We outline the recent progress in the development of methods that enable the radical α-C(sp3)–H functionalization of ketones, with an emphasis on radical initiation systems and possible mechanisms.
Org. Biomol. Chem., 2021,19, 7333-7347
https://doi.org/10.1039/D1OB01408K
CpxM(III)-catalyzed enantioselective C–H functionalization through migratory insertion of metal–carbenes/nitrenes
In this review, we highlight the developments in chiral CpxM(III) complexes or achiral CpxM(III) complexes/chiral carboxylic acid-catalyzed enantioselective C–H functionalization reactions through migratory insertion of metal–carbenes/nitrenes.
Org. Biomol. Chem., 2021,19, 7264-7275
https://doi.org/10.1039/D1OB01248G
Modern methods for the synthesis of perfluoroalkylated aromatics
This review summarizes the most recent organometallic, photochemical and electrochemical methods for the synthesis of perfluoroalkylated aromatic scaffolds, a family of compounds that is omnipresent in modern commercial and research applications.
Org. Biomol. Chem., 2021,19, 7116-7128
https://doi.org/10.1039/D1OB01122G
Unconventional approaches for the introduction of sulfur-based functional groups
Alternative solvents, ultrasound, electrochemistry and solvent-free methodologies to obtain sulfur-based compounds are herein reviewed. Special attention is paid to unconventional and/or sustainable processes.
Org. Biomol. Chem., 2021,19, 6926-6957
https://doi.org/10.1039/D1OB01091C
Silicon compounds in carbon-11 radiochemistry: present use and future perspectives
The use of silicon-based reagents and precursors for carbon-11 labelling has shown wide applicability and robustness with short reaction times using mild conditions. In this review, recent advances and future perspectives are examined.
Org. Biomol. Chem., 2021,19, 6916-6925
https://doi.org/10.1039/D1OB01202A
Silicon compounds as stoichiometric coupling reagents for direct amidation
This review covers all the reported use of stoichiometric silicon reagents for direct amidation of carboxylic acids with amines, commencing with the first example in 1969 up until April 2021.
Org. Biomol. Chem., 2021,19, 6746-6760
https://doi.org/10.1039/D1OB01003D
Advances in palladium-catalysed imidoylative cyclization of functionalized isocyanides for the construction of N-heterocycles
Palladium-catalysed isocyanide insertion reactions have witnessed great progress in recent years.
Org. Biomol. Chem., 2021,19, 6730-6745
https://doi.org/10.1039/D1OB00864A
Recent advances in the carbon–phosphorus (C–P) bond formation from unsaturated compounds by s- and p-block metals
A detailed discussion on the catalytic addition of P–H bonds from various phosphine reagents to unsaturated bonds for the C–P bond formation promoted by various s- and p-block metal catalysts is reported.
Org. Biomol. Chem., 2021,19, 6571-6587
https://doi.org/10.1039/D1OB01019K
Recent advances in the transition metal-free oxidative dehydrogenative aromatization of cyclohexanones
This review focuses on the transition metal-free oxidative dehydrogenative aromatization reactions of cyclohexanones, with an emphasis on the scope and limitations, as well as the mechanisms of these reactions.
Org. Biomol. Chem., 2021,19, 6380-6391
https://doi.org/10.1039/D1OB00908G
Utilization of ortho-alkynylarylcarbonyl derivatives for creating structurally diverse chemical compounds
ortho-Alkynylarylcarbonyl derivatives, due to their unique chemical reactivity, have been employed in widely divergent synthesis for the creation of cyclic and heterocyclic small-molecule libraries.
Org. Biomol. Chem., 2021,19, 5982-5998
https://doi.org/10.1039/D1OB00629K
Recent developments in asymmetric Heck type cyclization reactions for constructions of complex molecules
This review summarizes the recent developments in the asymmetric intramolecular Heck reaction and carbometallation-initiated cascade transformations including Ni-catalyzed processes with literature coverage mainly extending from 2016 to 2021.
Org. Biomol. Chem., 2021,19, 5673-5701
https://doi.org/10.1039/D1OB00496D
Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles
In this review, we describe the important advances in cycloaddition methodologies involving cyclopropanes for the construction of seven-, eight- and nine-membered carbocycles, with a particular attention to the variety of the mechanisms involved.
Org. Biomol. Chem., 2021,19, 5702-5724
https://doi.org/10.1039/D1OB00838B
Recent progress on electrochemical synthesis involving carboxylic acids
Recent progress on sustainable electrochemical synthesis involving carboxylic acids was reviewed.
Org. Biomol. Chem., 2021,19, 5501-5520
https://doi.org/10.1039/D1OB00420D
Recent developments in decarboxylative C(aryl)–X bond formation from (hetero)aryl carboxylic acids
This review highlights the recent developments in ipso-decarboxylative C–X (X = O/N/halo/S/Se/P/CN) bond formation using (hetero)aryl carboxylic acids, which are economical and environmentally benign starting materials.
Org. Biomol. Chem., 2021,19, 5476-5500
https://doi.org/10.1039/D1OB00675D
Thioxanthone: a powerful photocatalyst for organic reactions
Thioxanthone is a powerful photocatalyst. In this review, its photophysical properties and its applications in photopolymerisation and in organic synthesis are highlighted.
Org. Biomol. Chem., 2021,19, 5237-5253
https://doi.org/10.1039/D1OB00221J
Antitumor activity of tridentate pincer and related metal complexes
Pincer and related metal complexes containing tunable tridentate ligand frameworks display promising antitumor activity.
Org. Biomol. Chem., 2021,19, 5254-5273
https://doi.org/10.1039/D1OB00577D
Selected applications of Meldrum's acid – a tutorial
The overview describes synthetic routes towards substituted Meldrum's acids and its recent applications to inspire lab veterans and chemistry younglings.
Org. Biomol. Chem., 2021,19, 5014-5027
https://doi.org/10.1039/D1OB00395J
Recent progress in the nitration of arenes and alkenes
This mini review summarizes the recent advances in the regiospecific nitrations of arenes and alkenes based on the structural features of substrates.
Org. Biomol. Chem., 2021,19, 4835-4851
https://doi.org/10.1039/D1OB00384D
Recent advancements in the development of molecular organic photocatalysts
A review on the recent advances of six classes of organic photocatalysts with respect to photophysical and redox properties.
Org. Biomol. Chem., 2021,19, 4816-4834
https://doi.org/10.1039/D1OB00396H
Synthesis and stereoselective catalytic transformations of 3-hydroxyisoindolinones
This review highlights recent advancement in the synthesis of 3-hydroxyisoindolinones and their applications in stereoselective transformations.
Org. Biomol. Chem., 2021,19, 4637-4651
https://doi.org/10.1039/D1OB00164G
Advances of α-activated cyclic isothiocyanate for the enantioselective construction of spirocycles
α-Activated cyclic isothiocyanates featuring pharmacophores were efficient percusors for the enantioselective construction of intriguing spirocycles.
Org. Biomol. Chem., 2021,19, 4610-4621
https://doi.org/10.1039/D1OB00564B
Recent advances in the functionalization of polyfluoro(aza)aromatics via C–C coupling strategies
This review highlights the recent advances in the functionalization of polyfluoro(aza)aromatics via both transition metal-catalyzed and metal-free C–C coupling reactions for the period from 2006 to the beginning of 2021.
Org. Biomol. Chem., 2021,19, 4429-4459
https://doi.org/10.1039/D1OB00472G
Light-induced borylation: developments and mechanistic insights
This perspective delineates light-induced borylation methodologies, which have been developed in the last 10 years. Mechanistic insights have been explored throughout the article for these UV- and visible-light-induced borylation reactions.
Org. Biomol. Chem., 2021,19, 4397-4428
https://doi.org/10.1039/D1OB00323B
Catalytic asymmetric umpolung reactions of imines via 2-azaallyl anion intermediates
This review article describes all the significant recent developments in catalytic asymmetric umpolung reactions of imines involving a 2-azaallyl anion intermediate.
Org. Biomol. Chem., 2021,19, 4193-4212
https://doi.org/10.1039/D1OB00409C
Merging kinetic resolution with C–H activation: an efficient approach for enantioselective synthesis
This review summarizes the recent advancements in transition-metal (TM) catalyzed enantioselective C–H activation via kinetic resolution approach.
Org. Biomol. Chem., 2021,19, 4014-4026
https://doi.org/10.1039/D1OB00232E
Construction of bridged polycycles through dearomatization strategies
This review summarizes the-state-of-the-art advances of dearomatization strategies in the application of bridged ring formation.
Org. Biomol. Chem., 2021,19, 3960-3982
https://doi.org/10.1039/D1OB00096A
The transition-metal-catalyzed stereoselective ring-expansion of vinylaziridines and vinyloxiranes
This article covers ring expansions of vinylaziridines and vinyloxiranes developed over the past five years for accessing stereochemically enriched heterocycles.
Org. Biomol. Chem., 2021,19, 3776-3790
https://doi.org/10.1039/D1OB00259G
Enantioselective construction of the 8-azabicyclo[3.2.1]octane scaffold: application in the synthesis of tropane alkaloids
The 8-azabicyclo[3.2.1]octane core is the central motif of tropane alkaloids. This review compiles the methodologies employed to synthesize this scaffold in an enantioenriched form from achiral starting materials.
Org. Biomol. Chem., 2021,19, 3763-3775
https://doi.org/10.1039/D1OB00143D
Recent advances in the synthesis of pyrido[1,2-a]indoles
This review deals with the different accesses leading to the pyrido[1,2-a]indole nucleus in the last 20 years.
Org. Biomol. Chem., 2021,19, 3509-3526
https://doi.org/10.1039/D1OB00153A
Recent advances in the synthesis and reactivity of azetidines: strain-driven character of the four-membered heterocycle
Azetidines represent one of the most important four-membered heterocycles in organic synthesis. We provide an overview of the synthesis, reactivity and application of azetidines with a focus on the most recent advances, trends and future directions.
Org. Biomol. Chem., 2021,19, 3274-3286
https://doi.org/10.1039/D1OB00061F
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to synthetic methodology.