Themed collection Functionalization of unreactive C-H bonds
Photocatalytic functionalizations of alkynes
Visible light mediated functionalizations have significantly expanded the scope of alkynes by unraveling new mechanistic pathways and enabling their transformation to diverse structural entities.
Chain-walking reactions of transition metals for remote C–H bond functionalization of olefinic substrates
Transition metal-assisted remote C–H bond activation at the non-classical reaction sites of various olefinic substrates with the aid of a chain-walking process is depicted in this feature article.
Homogeneous catalytic C(sp3)–H functionalization of gaseous alkanes
The conversion of light alkanes into bulk chemicals is becoming an important challenge as it effectively avoids the use of prefunctionalized alkylating reagents.
Transition Metal Catalyzed C–H Bond Activation by exo-metallacycle Intermediates
C–H bond functionalization by high-valent cobalt catalysis: current progress, challenges and future perspectives
Over the last decade, high-valent cobalt catalysis has earned a place in the spotlight as a valuable tool for C–H activation and functionalization.
Iridium-catalyzed enantioselective addition of an N-methyl C–H bond to α-trifluoromethylstyrenes via C–H activation
Sterically Controlled C–H Alkenylation of Pyrroles and Thiophenes
Easy access to secondary and tertiary alcohols via metal-free and light mediated radical carbonyl allylation
An organo-photocatalyst catalyzed allylation of aryl ketones and aldehydes using readily available unactivated allylic substrates has been reported.
A soluble iron(II)-phthalocyanine-catalyzed intramolecular C(sp3)–H amination with alkyl azides
A soluble iron(II)-phthalocyanine, [FeII(tBu4Pc)(py)2], is an effective catalyst in intramolecular C(sp3)–H bond amination of alkyl azides to give the amination products in moderate to excellent yields with a broad substrate scope.
Co(III)-catalysed regioselective linear C(8)–H olefination of isoquinolone with terminal aromatic and aliphatic alkynes
A regioselective C8 linear olefination of isoquinoline-1H-2-one with terminal (aromatic and aliphatic) alkynes is reported under Co(III) catalysis.
Enantioselective first total syntheses of the antiviral natural products xiamycins D and E
The enantioselective first total syntheses of marine pentacyclic indolosesquiterpenoids xiamycins D (4) and E (5) have been described for the first time to the best of our knowledge.
Ruthenium(II)-catalyzed C–H activation and (4+2) annulation of aromatic hydroxamic acid esters with allylic amides
A (4+2) annulation under Ru(II)-catalysis is reported using aromatic hydroxamic acid esters as the oxidizing directing group and allylic amides as unactivated olefin coupling partners, delivering a wide variety of aminomethyl isoquinolinones in good to excellent yields.
Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy
It was found for the first time that transient directing group controlled regiodivergent CDC reactions at both sp2 and sp3 hybridized carbons of aromatic compounds with palladium catalyst.
Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C–H activation
An atroposelective Fujiwara–Moritani reaction towards the synthesis of alkenylthioglycoside is reported. β-thioglucose moiety is used both as a directing group for the C–H bond activation and as a chiral source inducing axial chirality.
Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C–H functionalization
Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer platforms were assembled to develop the demanding single-site heterogeneous ‘Pd(II)–NHC’-based oxidative C–H functionalization catalysts.
Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation
A new glycosylation method promoted by visible light with 3,5-dimethoxyphenyl glycoside as the donor was developed.
K2S2O8 activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
A diverse functionalization and synthesis of heterocycles using K2S2O8 as oxidant and glucose as persulfate activator in water at room temperature is reported.
Rhodium-catalysed direct formylmethylation using vinylene carbonate and sequential dehydrogenative esterification
A rhodium-catalysed direct formylmethylation adopting vinylene carbonate as an ethynol equivalent is reported.
Easy access to drug building-blocks through benzylic C–H functionalization of phenolic ethers by photoredox catalysis
A visible light-mediated photocatalyzed C–C-bond benzylic functionalization of phenolic ether-containing drug-like compounds is presented.
Z-Selective Pd-catalyzed 2,2,2-trifluoroethylation of acrylamides at room temperature
A straightforward methodology for the selective synthesis of high-value added Z-2,2,2-trifluoroethylated acrylamides by Pd-catalyzed C–H bond activation at room temperature.
Catalyst-controlled site-selective N–H and C3-arylation of carbazole via carbene transfer reactions
A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed.
Pd(II)-Catalyzed enantioselective arylation of unbiased methylene C(sp3)–H bonds enabled by a 3,3′-F2-BINOL ligand
Pd(II)-Catalyzed highly enantioselective arylation of unbiased methylene C(sp3)–H bonds using easily accessible 3,3′-F2-BINOL as a ligand was reported.
About this collection
The functionalization of unreactive carbon-hydrogen (C–H) bonds has evolved as an atom- and step-economical, environmentally benign strategy in organic synthesis. This themed collection deals with a wide range of strategies regarding the functionalization of unreactive C–H bonds by world-leading researchers in this field. The principal purpose of this collection is to illustrate the diversity of research on the functionalization of unreactive C–H bonds. Therefore, this special collection, Guest Edited by Tatiana Besset (University of Rouen), Fumitoshi Kakiuchi (Keio University), and Debabrata Maiti (Indian Institute of Technology-Bombay) includes: the development of new useful methodologies using base metal catalysts; various syntheses of functionalized compounds utilized in medicinal and materials chemistry; the utilization of renewable feedstock’s; employing electronic or optical energies for generating reactive intermediates; and synthetic processes towards industrial usages that have opened a new era for organic synthesis.