Palladium-Catalyzed Cross-Coupling of Aryl or Vinyl Iodides with Ethyl Diazoacetate.

(8E,10Z)-Tetradeca-8,10-dienal (1a), sex pheromone of the horse chestnut leafminer (Cameraria ohridella; Lepidoptera, Gracillariidae), and its geometrical isomers (1b-1d) were efficiently synthesized using tetrakis(triphenylphosphine)palladium catalyzed cross-coupling reactions of alk-1-ynes or alkenyl alanes with corresponding vinyl iodides. The stereoisomeric purity of obtained tetradecadienals 1a-1d was higher than 95% (GC). Relative electroantennographic (EAG) activities of the prepared compounds 1a-1d elicited on male antennae supported the previously published identification of the C. ohridella sex pheromone.

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Palladium-Catalyzed Cross Coupling Reactions of β-Iodo-β,γ-enones with Organozinc Chlorides

The Journal of Organic Chemistry ◽

10.1021/jo974001u ◽

1997 ◽

Vol 62 (6) ◽

pp. 1908-1908

Author(s):

Fen-Tair Luo ◽

Li-Chen Hsieh

Keyword(s):

Cross Coupling ◽

Coupling Reactions ◽

Cross Coupling Reactions ◽

Palladium Catalyzed

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Palladium catalyzed cross-coupling reactions of difunctional derivatives Bu3SnArBr. Synthesis of regioregular poly(3-alkylthiophenes) and poly(4-alkyl 2,2'-bithiophenes) with high molecular weights

Journal de Chimie Physique ◽

10.1051/jcp:1998259 ◽

1998 ◽

Vol 95 (6) ◽

pp. 1250-1253 ◽

Cited By ~ 5

Author(s):

J.-P. Lère-Porte ◽

J. J.E. Moreau ◽

C. Torreilles

Keyword(s):

Cross Coupling ◽

Coupling Reactions ◽

Molecular Weights ◽

Cross Coupling Reactions ◽

Regioregular Poly ◽

Palladium Catalyzed

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Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

10.26434/chemrxiv.12034743 ◽

2020 ◽

Author(s):

Aleksandra Balliu ◽

Aaltje Roelofje Femmigje Strijker ◽

Michael Oschmann ◽

Monireh Pourghasemi Lati ◽

Oscar Verho

Keyword(s):

Carboxylic Acid ◽

Building Blocks ◽

Wide Range ◽

Palladium Catalyzed ◽

Directing Group ◽

High Yields ◽

Vinyl Iodides ◽

Initial Results

In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both cis- and trans-configured carboxylic acid building blocks from the C–H alkenylation products.

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Suzuki–Miyaura cross-coupling for chemoproteomic applications

10.26434/chemrxiv.12055218.v1 ◽

2020 ◽

Author(s):

Jian Cao ◽

Ernest Armenta ◽

Lisa Boatner ◽

Heta Desai ◽

Neil Chan ◽

...

Keyword(s):

Mass Spectrometry ◽

Cross Coupling ◽

Protein Profiling ◽

Protein Labeling ◽

Caspase 8 ◽

Complex Cell ◽

Bioorthogonal Chemistry ◽

Reaction Conditions ◽

Target Deconvolution ◽

Palladium Catalyzed

Bioorthogonal chemistry is a mainstay of chemoproteomic sample preparation workflows. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on copper-catalyzed azide –alkyne cycloaddition (CuAAC) or 'click' chemistry. Here we demonstrate that gel-based activity-based protein profiling (ABPP) and mass-spectrometry-based chemoproteomic profiling can be conducted using Suzuki–Miyaura cross-coupling. We identify reaction conditions that proceed in complex cell lysates and find that Suzuki –Miyaura cross-coupling and CuAAC yield comparable chemoproteomic coverage. Importantly, Suzuki–Miyaura is also compatible with chemoproteomic target deconvolution, as demonstrated using structurally matched probes tailored to react with the cysteine protease caspase-8. Uniquely enabled by the observed orthogonality of palladium-catalyzed cross-coupling and CuAAC, we combine both reactions to achieve dual protein labeling.

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