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

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

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

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.

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

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.

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

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

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

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.

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

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

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.

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.

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.

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.

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

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

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

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

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.

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

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.

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.

(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.

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

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.

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