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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
[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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.