Themed collection New advances in catalytic C–C bond formation via late transition metals
Suzuki–Miyaura cross-couplings of secondary allylic boronic esters
The demonstration of a general method for cross-coupling of secondary allylic boronic esters was achieved for the first time under the same Pd-catalyzed conditions previously used for the coupling of benzylic substrates. Unlike allyl silanes, the regioselectivity of the arylation depends on the sterics and electronics of the allylic and vinylic substituents.
Ligand-guided pathway selection in nickel-catalyzed couplings of enals and alkynes
Simple variation of phosphine structure allows selective access to alkylative couplings or reductive cycloadditions.
Synthesis of chromans viaPd-catalyzed
alkene carboetherification reactions
Palladium-catalyzed cross-coupling reactions between 2-(but-3-enyl)phenols and aryl or alkenyl bromides provide straightforward access to substituted chroman derivatives.
Two-stage optimization of a supramolecular
catalyst for catalytic asymmetric hydroboration
Systematic changes, first to the catalyst scaffold and then to the ligating groups, are successfully used to fine tune supramolecular catalyst structures.
Selective formation of angular tricyclic compounds by ruthenium-mediated ring-rearrangement metathesis
Angular tricyclic compounds with a variety of ring-sizes were produced by ring-rearrangement metathesis, sometimes with a high degree of selectivity.
Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides
A protocol based on a Pd(OAc)2/SPhos catalyst system for the Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides that minimizes protodeboronation is described.
Regioselective C–H bond functionalizations of
acridines using organozinc reagents
Regioselective C–H bond arylation and alkylation of acridines using organozinc reagents are described.
1,2,3-triazole-fused heterocycles viaPd-catalyzed cyclization of 5-iodotriazoles
A concise synthesis of fused 1,2,3-triazoles is described, featuring a palladium-catalyzed intramolecular Heck or direct arylation reaction.
benzylation and arylation of nitriles
Decarboxylative coupling of benzylic and heterobenzylic esters results in either benzylation or arylation of nitrile-stabilized anions.
Synthesis of diaryl ketonesvia a
phosphine-free Fukuyama reaction
An efficient method to form unsymmetrical diaryl ketones via Fukuyama cross-coupling reactions with low loadings of Pd(dba)2 has been developed.
carbonylation of benzamides with carbon monoxide
A mild Rh-catalyzed carbonylative coupling of benzamides to form phthalimides has been developed.
Pyridine synthesis from oximes and alkynesviarhodium(III) catalysis: Cp* and Cpt provide complementary selectivity
The use of sterically different ligands in the synthesis of pyridines from oximes and alkynes allows for complementary selectivities to be achieved.
Regiocontrolled aerobic oxidative coupling of
indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands
Diazafluorene-derived ligands enable regiocontrolled Pd-catalyzed oxidative coupling of indoles and benzene to proceed with O2 as the oxidant.
Cobalt-catalyzed conjugate addition of silylacetylenes to α,β-unsaturated ketones
Catalytic addition of silylacetylenes to α,β-unsaturated ketones proceeded in the presence of a cobalt complex coordinated with a bisphosphine ligand to give high yields of β-alkynylketones.
Catalytic enantioselective Grignard Nozaki–Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability
Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki–Hiyama methallylations from the alcohol or aldehyde oxidation level via iridium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetate does not react efficiently.
Synthesis of epoxybenzo[d]isothiazole 1,1-dioxides via a reductive-Heck, metathesis-sequestration protocol
An atom-economical, purification free method for the synthesis of tricyclic sultams has been developed utilizing a facilitated ring-opening metathesis polymerization (ROMP) protocol.
alkenyl- and arylsilylation reactions forming 1-silaindenes
In the presence of gold(I)–phosphine catalysts, alkenyl- and arylsilanes undergo intramolecular cyclisation reactions onto appendant alkyne moieties to afford 1-silaindene derivatives. The reaction pathways vary depending on the substituent on silicon.
Control of selectivity in the generation and reactions of oxonium ylides
trans-6-Aryl-4-keto-2-pyranyl-diazoacetoacetates undergo the [1,2]-Stevens rearrangement in a controllable conformation-dependent process.
palladium-catalyzed N-arylation of a sulfoximine with aryl chlorides
Aryl chlorides are useful substrates for the palladium-catalyzed N-arylation of a sulfoximine when RuPhos is used as a ligand.
Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes
2-Alkylindoles are prepared regiospecifically in a gold-catalyzed bimolecular process under exceedingly mild reaction conditions.
hydroboration of β,γ-unsaturated Weinreb amides: striking influence of the borane
Subtle differences in borane structure strongly influence the efficiency of catalytic asymmetric hydroboration with β,γ-unsaturated Weinreb amide substrates.
A highly active and selective palladium pincer
catalyst for the formation of α-aryl ketonesvia cross-coupling
The air and moisture stable Pd complex [t-BuPhebox-Me2]PdBr is capable of efficiently promoting α-monoarylation of ketones with numerous aryl bromides in 1 h at 70 °C with 82–99% yields.
Solvent controlled mechanistic dichotomy in a Au(III)-catalyzed, heterocyclization triggered, Nazarov reaction
Tandem Au(III)-catalyzed heterocyclization/Nazarov cyclizations leading to substituted carbocycle fused furans are described. An interesting dichotomy of reaction pathways as a function of solvent, confirmed by the isolation and trapping of reaction intermediates, provided a basis for computational studies that supported the experimental findings.
Pd(II)-catalyzed decarboxylative cross-coupling of oxamic acids with potassium phenyltrifluoroborates under mild conditions
A novel Pd-catalyzed decarboxylative cross-coupling of oxamic acids with potassium phenyltrifluoroborates has been realized under mild reaction conditions.
Pd(0)/Au(I) redox incompatibilities as revealed by Pd-catalyzed homo-coupling of arylgold(I)-complexes
A Pd(0)/Au(I) redox-driven palladium catalyzed homo-coupling of gold–aryl complexes illustrates potential redox incompatibilities of both metals for the development of Pd/Au dual catalysis.
Increasing synthetic efficiency via direct C–H functionalization: formal synthesis of an
inhibitor of botulinum neurotoxin
A new synthesis of an inhibitor of botulinum neurotoxin is reported which involves the formal activation of three C–H bonds.
Highly efficient desymmetrisation of a tricarbonylchromium 1,4-dibromonaphthalene complex by asymmetric Suzuki–Miyaura coupling
An efficient protocol is described for the desymmetrisation of a prochiral complex by catalytic desymmetrisation via an asymmetric Suzuki–Miyaura coupling reaction, using a bulky chiral palladium catalyst.
Nickel-catalyzed intermolecular codimerization of acrylates and alkynes
The codimerization of acrylates and alkynes to produce 1,3-dienes is demonstrated using a nickel catalyst in association with 2-aminopyridine.
Room-temperature nickel-catalysed cross-couplings of aryl chlorides with arylzincs
P,N,O-chelate nickel complexes efficiently catalyse the cross-coupling reaction of arylzinc reagents with aryl chlorides at room temperature with low catalyst loading.
Gold(I)-catalysed synthesis of conjugated trienes
Gold(I)-catalysed reaction between cyclopropenes and furans produces functionalised conjugated trienes.
Preparation of benzolactams by Pd(II)-catalyzed
carbonylation of N-unprotected arylethylamines
An unprecedented NH2-directed Pd(II)-catalytic carbonylation of quaternary N-unprotected arylethylamines to yield selectively 6-membered benzolactams has been developed.
Acetoxypalladation of unactivated
alkynes and capture with alkenes to give 1-acetoxy-1,3-dienes taking dioxygen as terminal oxidant
A general protocol for the synthesis of 1-acetoxy-1,3-dienes from alkynes and alkenes by an acetoxypalladation/Heck cross-coupling/β-H elimination tandem process is described.
coupling reaction of aryl(trialkyl)silanes with aryl chlorides and tosylates
Nickel-catalysed cross-coupling reactions of aryl(trialkyl)silanes with aryl chlorides and tosylates are described.
About this collection
The invited, peer-reviewed articles in this web themed issue highlight cutting-edge contributions by international leaders and celebrate current achievements and future perspectives in this exciting field of research.
The guest editor of this issue is Michael Krische (University of Texas at Austin).
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