Solid-Phase Synthesis and Catalytic Screening of Polystyrene Supported Diphosphines

Samuels, Michiel C.; Heutz, Frank J. L.; Grabulosa, Arnald; Kamer, Paul C. J.

doi:10.1007/s11244-016-0700-1

Cited by 7 publications

(3 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…To achieve this, we designed a polystyrene-cross-linking bisphosphine PS-DPPBz (Chart ). The rigid 1,2-bis(diphenylphosphino)benzene (DPPBz) core was adopted as the bisphosphine unit to achieve reliable metal chelation ability in a polymer matrix. − The steric demand in proximity to the P atoms should be only moderate (DPPBz-like) due to the spacer effect of the four aromatic rings on the P atoms, which form a pyramidal-type space; and consequently, the resulting P–P-chelated metal system should provide effective access of substrates for catalysis.…”

Section: Resultsmentioning

confidence: 99%

A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis

et al. 2017

View full text Add to dashboard Cite

A polystyrene-cross-linking bisphosphine PS-DPPBz was synthesized through radical emulsion copolymerization between 4-t-butylstyrene as a monomer and tetravinylated 1,2-bis(diphenylphosphino)benzene (DPPBz) as a 4-fold cross-linker. The location of the DPPBz bisphosphine moiety at the branching points of the cross-linked network organic polymer allowed controlled bisphosphine monochelation to transition metals under conditions where homogeneous ligands may form bischelated single metal complexes or multinuclear complexes. PS-DPPBz showed high ligand performance in firstrow transition metal catalysis, enabling challenging molecular transformations that were not possible through the screening of existing homogeneous ligands. In the Ni-catalyzed amination of aryl chlorides with N-alkyl-substituted primary amines, the substrate scope has been expanded to include 2,6-disubstituted aryl chlorides and N-tertiary-alkyl-substituted primary amines. PS-DPPBz was effective for the Ni-catalyzed C−H/C−O coupling between 1,3-azoles and monocyclic aryl pivalates, which showed poor reactivity in the reported homogeneous catalytic system based on 1,2-bis(dicyclohexylphosphino)ethane (DCYPE). The usefulness of the polymer-cross-linking strategy was also demonstrated in alkene hydroboration reactions catalyzed by Cu or Co.

show abstract

Section: Resultsmentioning

confidence: 99%

A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis

et al. 2017

View full text Add to dashboard Cite

show abstract

“…51,62 The secondary phosphines 1a-d immobilized on Merrield resin cross-linked with 1% and 4% divinylbenzene (DVB, MF), JandaJel™ resin (JJ) and polystyrene (PS) were prepared as we reported previously. 63,64 Deprotonation of 1a-d by using an excess of lithium diisopropylamide (LDA) yielded the corresponding supported lithium phosphides (Scheme 1, step 1).…”

Section: Solid-phase Synthesis Of Supported Triphos Ligandsmentioning

confidence: 99%

Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction

et al. 2019

View full text Add to dashboard Cite

show abstract

“…40) Für natürliche Porphyrine gibt es neue Anwendungen und Konzepte. Hämproteine, die in der Natur nicht vorkommen, können C-H-Insertionsreaktionen katalysieren, wenn 44) Neue Methoden für die organische Synthese an der festen Phase (SPOS) sind die goldkatalysierte Synthese von Imidazolin-2-onen, 45) die Synthese von Phosphinen 46) und die On-resin-Makrocyclisierung von Peptiden via Ugi-Smiles-Multikomponentenreaktion 47) oder Alkinmetathese. 48) Murelli und Mitarbeiter synthetisierten durch Oxidopyrylium-Cycloaddition an der festen Phase eine Bibliothek von α-Hydroxytropolonen (47), die sich spurlos ablösen ließen (Abbildung 16 Mitte).…”

Section: Organische Farbstoffeunclassified

Message in a molecule

et al. 2016

View full text Add to dashboard Cite

Since ancient times, steganography, the art of concealing information, has largely relied on secret inks as a tool for hiding messages. However, as the methods for detecting these inks improved, the use of simple and accessible chemicals as a means to secure communication was practically abolished. Here, we describe a method that enables one to conceal multiple different messages within the emission spectra of a unimolecular fluorescent sensor. Similar to secret inks, this molecular-scale messaging sensor (m-SMS) can be hidden on regular paper and the messages can be encoded or decoded within seconds using common chemicals, including commercial ingredients that can be obtained in grocery stores or pharmacies. Unlike with invisible inks, however, uncovering these messages by an unauthorized user is almost impossible because they are protected by three different defence mechanisms: steganography, cryptography and by entering a password, which are used to hide, encrypt or prevent access to the information, respectively.

show abstract

Solid-Phase Synthesis and Catalytic Screening of Polystyrene Supported Diphosphines

Cited by 7 publications

References 50 publications

A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis

A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis

Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction

Message in a molecule

Contact Info

Product

Resources

About