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Themed collection Chemistry Nobel 2010 Web Collection: Cross-coupling reactions in organic chemistry

28 items
Perspective

π-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(II)

Alkene ligands exert interesting properties on Pd(0) and Pd(II) species, which can be exploited in catalytic processes.

Graphical abstract: π-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(ii)
Perspective

The Heck–Mizoroki cross-coupling reaction: a mechanistic perspective

Recent advances in the study of the mechanism of the Heck–Mizoroki reaction are presented and discussed.

Graphical abstract: The Heck–Mizoroki cross-coupling reaction: a mechanistic perspective
Emerging Area

Cross-coupling reactions of nucleoside triphosphates followed by polymerase incorporation. Construction and applications of base-functionalized nucleic acids

Novel construction of base-functionalized nucleic acids consisting in cross-coupling reactions of nucleoside triphosphates followed by polymerase incorporation is presented within the context of a minireview on enzymatic synthesis of base-modified DNA and RNA.

Graphical abstract: Cross-coupling reactions of nucleoside triphosphates followed by polymerase incorporation. Construction and applications of base-functionalized nucleic acids
Communication

Platinum-catalyzed cross-dehydrogenative coupling reaction in the absence of oxidant

A third strategy for cross-dehydrogenative coupling reaction has been reported via platinum catalysis in the absence of oxidant.

Graphical abstract: Platinum-catalyzed cross-dehydrogenative coupling reaction in the absence of oxidant
Communication

Nickel-catalyzed cross-coupling of diarylamines with haloarenes

The cross-coupling reaction of diarylamines with aryl bromides/iodides can be effected by the Ni(II)–(σ-aryl) complex/PPh3/NaH system, and a preliminary investigation was conducted into the mechanism of this reaction.

Graphical abstract: Nickel-catalyzed cross-coupling of diarylamines with haloarenes
Communication

Fluoride-free cross coupling using vinyldisiloxanes

Vinyldisiloxanes equilibrate with the corresponding silanolates under basic conditions and subsequently undergo palladium catalysed cross coupling with aryl/heteroaryl iodides and bromides.

Graphical abstract: Fluoride-free cross coupling using vinyldisiloxanes
Communication

Palladium-catalyzed decarboxylative cross-coupling reaction of cinnamic acid with aryl iodide

A highly effective decarboxylative cross-coupling reaction of cinnamic acid with aryl iodide catalyzed by the combination of palladium chloride and CyJohnPhos is described.

Graphical abstract: Palladium-catalyzed decarboxylative cross-coupling reaction of cinnamic acid with aryl iodide
Communication

Suzuki–Miyaura cross-coupling reaction catalyzed by Pd/MgLa mixed oxide

A new, reusable Pd/MgLa mixed oxide catalyst has been applied successfully to the Suzuki–Miyaura carbon–carbon cross-coupling reaction.

Graphical abstract: Suzuki–Miyaura cross-coupling reaction catalyzed by Pd/MgLa mixed oxide
Communication

Facile synthesis of multisubstituted buta-1,3-dienes via Suzuki–Miyaura and Kumada cross-coupling strategy of 2,4-diiodo-buta-1-enes with arylboronic acids and Grignard reagents

One-pot Suzuki–Miyaura-type and Kumada-type cross-coupling reactions of 2,4-diiodo-buta-1-enes with arylboronic acids and alkyl/aryl magnesium bromides were carried out in the presence of accessibly simple catalysts under mild conditions.

Graphical abstract: Facile synthesis of multisubstituted buta-1,3-dienes via Suzuki–Miyaura and Kumada cross-coupling strategy of 2,4-diiodo-buta-1-enes with arylboronic acids and Grignard reagents
Communication

Tandem one pot asymmetric conjugate addition–vinyl triflate formation–cross coupling methodology

Optically active vinyl triflates are obtained and employed in a series of one pot metal-catalyzed tandem asymmetric transformations.

Graphical abstract: Tandem one pot asymmetric conjugate addition–vinyl triflate formation–cross coupling methodology
Communication

Exploiting the palladium[0]-catalysed Ullmann cross-coupling reaction in natural products chemistry: application to a total synthesis of the alkaloid (±)-aspidospermidine

Azide 14, available through the title cross-coupling process, has been converted, via the ring-fused aziridine 15, into the alkaloid aspidospermidine.

Graphical abstract: Exploiting the palladium[0]-catalysed Ullmann cross-coupling reaction in natural products chemistry: application to a total synthesis of the alkaloid (±)-aspidospermidine
Paper

Cross-coupling reaction of alcohols for carbon–carbon bond formation using pincer-type NHC/palladium catalysts

A cross-coupling reaction of different alcohols was achieved using a pincer-type NHC/PdBr complex as the catalyst precursor, and the reaction, under either Ar or H2 gas, displayed a broad substrate scope with respect to both primary and secondary alcohol components, with high product alcohol selectivity.

Graphical abstract: Cross-coupling reaction of alcohols for carbon–carbon bond formation using pincer-type NHC/palladium catalysts
Paper

[2.2]Paracyclophane-based monophosphine ligand for palladium-catalyzed cross-coupling reactions of aryl chlorides

A bulky, electron-rich monophosphine has been prepared, showing excellent performance in the Pd-catalyzed Buchwald–Hartwig amination and Suzuki–Miyaura coupling reaction of aryl chlorides, including deactivated ones.

Graphical abstract: [2.2]Paracyclophane-based monophosphine ligand for palladium-catalyzed cross-coupling reactions of aryl chlorides
Paper

New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles

The Suzuki methodology was found to be the most effective palladium catalyzed cross-coupling reaction to synthesize in few steps enantiomerically pure 2-propylsuccinyl imidazole derivatives from chiral alkenyl boronate esters.

Graphical abstract: New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles
Paper

N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine: a highly active, practical and versatile catalyst for the Heck–Mizoroki reaction

An easily prepared, air- and moisture-stable, well-defined NHC-palladacycle mediates the single and double Heck–Mizoroki reaction of a number of functionalized aryl bromides, iodides and triflates with acrylic esters, amides and styrene derivatives in good to excellent yields.

Graphical abstract: N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine: a highly active, practical and versatile catalyst for the Heck–Mizoroki reaction
Paper

Trifluoromethyl-substituted pyridyl- and pyrazolylboronic acids and esters: synthesis and Suzuki–Miyaura cross-coupling reactions

Highly-functionalised pyridine and pyrazole derivatives incorporating trifluoromethyl substituents have been synthesised by Suzuki–Miyaura cross-coupling protocols.

Graphical abstract: Trifluoromethyl-substituted pyridyl- and pyrazolylboronic acids and esters: synthesis and Suzuki–Miyaura cross-coupling reactions
Paper

Alcohol cross-coupling reactions catalyzed by Ru and Ir terpyridine complexes

Primary alcohols can be coupled with secondary benzylic alcohols by an air-stable catalytic system involving terpyridine ruthenium or iridium complexes.

Graphical abstract: Alcohol cross-coupling reactions catalyzed by Ru and Ir terpyridine complexes
Paper

Phosphinates as new electrophilic partners for cross-coupling reactions

Lactam derived enol phosphinates are novel viable electrophiles in Suzuki–Miyaura and Stille cross-coupling reactions.

Graphical abstract: Phosphinates as new electrophilic partners for cross-coupling reactions
Paper

Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids

Allylic alcohols can be used directly for the palladium-catalyzed allylation of aryl- and alkenylboronic acids without the aid of a base.

Graphical abstract: Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids
Paper

Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations

Synthesis of novel purine bases and nucleosides bearing unsubstituted or substituted cyclopropyl rings in position 6 is reported. 6-Cyclopropylpurine ribonucleoside exerted a significant cytostatic effect while all substituted derivatives were inactive.

Graphical abstract: Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations
Paper

Synthesis of 2′-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions

Title 2′-deoxyadenosine derivatives bearing bipyridine, phenanthroline or terpyridine ligands and their RuII-complexes in position 8 were prepared by cross-couplings of 8-bromoadenosine with acetylene or boronate derivatives of oligopyridine ligands or Ru complexes.

Graphical abstract: Synthesis of 2′-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions
Paper

Efficient Heck reactions catalyzed by a highly recyclable palladium(II) complex of a pyridyl-functionalized imidazolium-based ionic liquid

A series of pyridyl-functionalized imidazolium-based ionic liquids with high thermal stability and wide liquid range were synthesized. Heck cross-coupling reactions catalyzed by a Pd(II)-containing ionic liquid complex in the corresponding ionic liquid shows high recyclability.

Graphical abstract: Efficient Heck reactions catalyzed by a highly recyclable palladium(ii) complex of a pyridyl-functionalized imidazolium-based ionic liquid
Paper

Insights into the mechanism of the site-selective sequential palladium-catalyzed cross-coupling reactions of dibromothiophenes/dibromothiazoles and arylboronic acids. Synthesis of PPARβ/δ agonists

A reactivity study, aided by NMR spectroscopy, leads to conclusions regarding aspects like positional selectivity and rate-limiting steps. Additionally, trisubstituted thiophene derivatives with PPARβ/δ agonist activity have been synthesized.

Graphical abstract: Insights into the mechanism of the site-selective sequential palladium-catalyzed cross-coupling reactions of dibromothiophenes/dibromothiazoles and arylboronic acids. Synthesis of PPARβ/δ agonists
Paper

Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines

(Adenin-8-yl)phenylalanine base, nucleosides, nucleotides and nucleoside triphosphates, as well as (purin-6-yl)phenylalanine base and nucleosides were prepared by aqueous-phase Pd-catalysed cross-coupling reactions.

Graphical abstract: Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines
Paper

Copper(I) mediated cross-coupling of amino acid derived organozinc reagents with acid chlorides

A user-friendly protocol for the copper(I) mediated cross-coupling of acid chlorides with organozinc reagents derived from amino acids.

Graphical abstract: Copper(i) mediated cross-coupling of amino acid derived organozinc reagents with acid chlorides
Paper

Synthesis and electronic properties of series of oligothiophene-[1,10]phenanthrolines

Synthesis of a variety of oligothiophene-substituted [1,10]phenanthrolines in good overall yields and purities by Pd-catalyzed Negishi cross-coupling reactions of iodinated phenanthrolines and zincated oligothiophenes.

Graphical abstract: Synthesis and electronic properties of series of oligothiophene-[1,10]phenanthrolines
Paper

Dye-functionalized head-to-tail coupled oligo(3-hexylthiophenes)—perylene–oligothiophene dyads for photovoltaic applications

Novel donor–acceptor hybrid molecules, consisting of head-to-tail coupled oligo(3-hexylthiophene)s covalently linked to perylenemonoimide, were synthesized and structure–property relationships established.

Graphical abstract: Dye-functionalized head-to-tail coupled oligo(3-hexylthiophenes)—perylene–oligothiophene dyads for photovoltaic applications
Paper

An exploration of Suzuki aryl cross coupling chemistry involving [2.2]paracyclophane derivatives

An examination into the scope and limitations of Suzuki aryl cross coupling chemistry using derivatives of [2.2]paracyclophane is described.

Graphical abstract: An exploration of Suzuki aryl cross coupling chemistry involving [2.2]paracyclophane derivatives
28 items

About this collection

To commemorate the 2010 Nobel Prize for Chemistry awarded to Heck, Negishi and Suzuki for their contributions to Pd-catalised cross coupling reactions in organic synthesis we have put together a collection of some of the Organic & Biomolecular Chemistry articles recently published on this groundbreaking subject.

Congratulations to these three pioneers of organic chemistry.

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