Contributors to the 1st Emerging Investigators collection
Organic Chemistry Frontiers profiles the contributors to the “Emerging Investigators” themed collection.
Recent advances in transition metal-catalysed hydroacylation of alkenes and alkynes
This highlight presents advances in transition metal-catalysed alkene and alkyne hydroacylation over the past three years.
Photoredox sheds new light on nickel catalysis: from carbon–carbon to carbon–heteroatom bond formation
Recent emergence of photoredox/nickel dual catalysis to generate carbon–carbon and carbon–heteroatom bonds is highlighted.
A remarkable solvent effect of fluorinated alcohols on transition metal catalysed C–H functionalizations
Fluorinated solvents like 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and trifluoroethanol (TFE) have recently emerged as a remarkable synthetic hint allowing challenging C–H activation reactions.
Non-covalent organocatalysis in asymmetric oxidative C(sp3)–H bond functionalization – broadening C–H bond coupling reactions
In this highlight, the design of cooperative non-covalent organocatalysis for the development of novel asymmetric oxidative C–H bond functionalization reactions is presented.
The quest for observation and isolation of oxyallyl derivatives
This review summarizes 50 years of attempts to observe, and finally isolate, the elusive oxyallyl derivatives.
Gold-catalyzed bis(stannylation) of propiolates
Bis(stannylation) of propiolates with hexabutylditin is achieved under mild conditions using a cationic gold(I) catalyst.
Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone
A series of novel chiral monophosphine ligands Xiang-Phoses were designed and have been applied to the enantioselective gold-catalyzed intermolecular [2 + 2]-cycloaddition of 3-styrylindoles 1 with N-allenyl oxazolidinone 2.
Low-valent cobalt-catalyzed C–H allylation
A mild C–H allylation promoted by a cobalt salt combined with a Grignard reagent is described.
Hydroamination of alkenyl N-arylhydrazones mediated by t-BuOK for the synthesis of nitrogen heterocycles
The t-BuOK-mediated reactions of γ,δ-alkenyl hydrazones enabled intramolecular hydroamination with the outer nitrogen, affording tetrahydropyridazine derivatives.
Transformable nanostructures of cholesteryl-containing rhomboidal metallacycles through hierarchical self-assembly
Various interesting nanostructures such as flowers and tadpole shaped structures were successfully obtained from well-defined cholesteryl-containing rhomboidal metallacycles prepared by coordination-driven self-assembly.
Allylic borylation of tertiary allylic alcohols: a divergent and straightforward access to allylic boronates
A novel method for the preparation of diverse allylic boronates from simple allylic alcohols is reported.
Palladium-catalyzed arylation of β-methylene C(sp3)–H bonds at room temperature: desymmetrization of simple cycloalkyl carboxylic acids
A new protocol for Pd-catalyzed β methylene C–H arylation of N-quinolyl cycloalkylcarboxamides with aryl iodides at room temperature is reported.
Ruthenium-catalyzed selective imine synthesis from nitriles and secondary alcohols under hydrogen acceptor- and base-free conditions
Ruthenium-catalyzed selective imine synthesis from nitriles and secondary alcohols under hydrogen acceptor- and base-free conditions was achieved.
Palladium-catalyzed phosphonyldifluoromethylation of alkenes with bromodifluoromethylphosphonate
An efficient palladium-catalyzed phosphonyldifluoromethylation of alkenes with bromodifluoromethylphosophonate is described. The method provides a facile access to a series of phosphonyldifluoromethylated alkenes that are of interest in medicinal chemistry. Mechanistic studies reveal that a phosphonyl difluouromethyl radical is involved in the reaction.
Synthesis of 1,1-diboronate esters by cobalt-catalyzed sequential hydroboration of terminal alkynes
Co-catalyzed sequential hydroborations of alkyl and aryl alkynes with pinacolborane produce 1,1-diboronate esters with high selectivity and yields.
Visible-light promoted intermolecular halofunctionalization of alkenes with N-halogen saccharins
A simple and efficient visible-light promoted intermolecular haloamination and haloetherification of alkenes was reported.
Pd(II)-catalyzed β-C–H arylation of O-methyl ketoximes with iodoarenes
A Pd(II)-catalyzed selective β-arylation of O-methyl ketoximes was developed using iodoarenes as the coupling partners.
A photo-induced C–C bond formation methodology to construct tetrahydrofluorenones and their related structures
A metal-free, photo-induced C–C bond formation methodology was developed to construct tetrahydrofluorenones and their related structures.
A concise total synthesis of sespenine, a structurally unusual indole terpenoid from Streptomyces
A ten-step (the longest linear sequence) total synthesis of sespenine was accomplished.
Iodine(III)-mediated oxidative intramolecular arene–alkene coupling exemplified in the synthesis of phenanthrenes
A novel iodine(III)-mediated synthesis of substituted phenanthrenes from ortho-vinylated biaryl derivatives through 6-endo-trig selective oxidative intramolecular arene–alkene coupling is reported.
N-Heterocyclic carbene catalyzed dehydrogenative coupling of enals: synthesis of monobactams
The novel NHC-catalyzed dehydrogenative coupling of enals is described to generate a wide range of monobactams.
Gold-catalyzed tandem synthesis of bioactive spiro-dipyrroloquinolines and its application in the one-step synthesis of incargranine B aglycone and seneciobipyrrolidine (I)
The Au-catalyzed tandem reaction provided simple and efficient access to spiro-dipyrroloquinolines and incargranine B aglycone and (±)-seneciobipyrrolidine (I).
Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters
Dearomative cycloadditions of imino esters derived from alanine with 3-nitroindoles form exo′-pyrroloindolines in good yields with high diastereo- and enantioselectivities.
Pd/norbornene-catalyzed sequential ortho-C–H alkylation and ipso-alkynylation: a 1,1-dimethyl-2-alkynol strategy
A palladium/norbornene-catalyzed ortho-C–H alkylation and ipso-alkynylation reaction for the synthesis of 2-alkyl-1-alkynyl arenes was reported, where the use of bulky 1,1-dimethyl-2-alkynols led to significant suppression of the formation of O-alkylation and norbornene alkynylation by-products.
Exploiting ortho-substitution effect on formation of oxygen-containing paracyclophane through ring-closing metathesis
The synthesis of strained paracyclophanes is facilitated by ortho-substitution effect on phenyl ring.
A novel zinc based binary catalytic system for CO2 utilization under mild conditions
A novel zinc based binary catalytic system for the synthesis of cyclic carbonates under mild and solvent-free conditions utilizing CO2 as a C1 building block is reported.
Rhenium and base co-catalyzed [3 + 2] annulations of N–H ketimines and alkynes to access unprotected tertiary indenamines through C–H bond activation
A rhenium and base co-catalyzed [3 + 2] carbocyclization of N–H ketimines and alkynes through C–H bond activation is developed.
Palladium-catalysed coupling reaction of aminals with N-sulfonyl hydrazones to give allylic sulfones
Palladium-catalysed cross-coupling of aminals with N-sulfonyl hydrazones has been established via C–N bond activation under base-free conditions.
Studies towards the synthesis of the functionalized C3–C14 decalin framework of alchivemycin A
Herein, we report our synthetic endeavors towards the synthesis of the C3–C14 fragment of the complex natural product alchivemycin A.
Glycosylation via remote activation of anomeric leaving groups: development of 2-(2-propylsulfinyl)benzyl glycosides as novel glycosyl donors
New glycosyl donors with recyclable and regenerable leaving groups, which could be activated via remote mode, were designed for latent-active glycosylation.
Synthesis of isoxazoline-featured oxindoles by iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of alkenes
Isoxazoline-featured oxindoles were synthesized by the reaction of β,γ-unsaturated ketoximes with N-arylacrylamides via iminoxyl radical-promoted cascade intra/intermolecular oxyalkylation/alkylarylation of alkenes.
Palladium-catalyzed decarboxylative alkoxycarbonylation of potassium aryltrifluoroborates with potassium oxalate monoesters
An efficient method for the preparation of aryl esters has been developed via Pd-catalyzed decarboxylative coupling of potassium aryltrifluoroborates and potassium oxalate monoesters.
Copper-catalyzed aminotrifluoromethylation of alkenes: a facile synthesis of CF3-containing lactams
Copper-catalyzed aminotrifluoromethylation of alkenes has been achieved using amides as nucleophiles to provide valuable CF3-containing lactams in good yields under mild conditions.
Palladium-catalyzed C(sp3)–H arylation of lactic acid: efficient synthesis of chiral β-aryl-α-hydroxy acids
A palladium-catalyzed oxidative arylation of lactic acid is described.
Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B
Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B is described. The heteroaromatic core of the natural products was assembled using a one-pot benzylic oxidation–oxidative heterocyclization process.
Employing carboxylic acids in aryne multicomponent coupling triggered by aziridines/azetidines
The transition-metal-free aryne multicomponent coupling (MCC) involving carboxylic acids initiated by aziridines/azetidines leading to the synthesis of N-aryl β/γ-amino alcohol derivatives has been developed.
Fluorescent nanoassemblies between tetraphenylethenes and sulfonatocalixarenes: a systematic study of calixarene-induced aggregation
We demonstrated a systematic study of calixarene-induced aggregation (CIA) that how and to what extent the structures of hosts and guests affect the assembly behavior by fluorescence spectroscopy.
Regioselective palladium(II)-catalyzed aerobic oxidative Heck-type C3 alkenylation of sulfocoumarins
An efficient method for the direct C–H olefination of sulfocoumarins with a wide range of alkenes is developed. Moreover, O2 was successfully utilized as the sole oxidant for the oxidative Heck reaction. This approach enables the rapid generation of various 3-alkenylated sulfocoumarins.
Blue AIE luminogens bearing methyl groups: different linkage position, different number of methyl groups, and different intramolecular conjugation
By changing the linkage position and linked number of the methyl group, the resultant AIE luminogens demonstrated adjustable intramolecular conjugation.
γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines
1,3,5-Substituted pyrrolidin-2-ones were synthesised via an iodine mediated cyclisation of 3-methyl substituted homoallylamines in good to excellent yield, as mixtures of diastereoisomers. Furan bispyrrolidines were formed as single diastereoisomers when 3-phenyl homoallylamines were employed in an analogous reaction.
Palladium-catalyzed methylene C(sp3)–H arylation of the adamantyl scaffold
A palladium-catalyzed C(sp3)–H arylation of adamantane at the methylene position with the assistance of an amide group was developed.
About this collection
Welcome to the inaugural Emerging Investigators themed collection of Organic Chemistry Frontiers. It showcases the high quality research of up-and-coming researchers working at the forefront of organic chemistry science.