Pd-Diimine: A Highly Selective Catalyst System for the Base-Free Oxidative Heck Reaction

Gottumukkala, Aditya L.; Teichert, Johannes F.; Heijnen, Donis; Eisink, Niek N. H. M.; Dijk, Simon van; Ferrer, Catalina; Hoogenband, Adri van den; Minnaard, Adriaan J.

doi:10.1021/jo101942f

Cited by 88 publications

(51 citation statements)

References 28 publications

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.63–7.56 (d, J = 16.1 Hz, 1H), 7.55–7.49 (m, 2H), 7.42–7.34 (m, 3H), 6.41–6.35 (d, J = 16.1 Hz, 1H), 1.55 (s, 9H). 39 …”

Section: Methodsmentioning

confidence: 99%

“Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature

2014

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The third generation designer amphiphile/surfactant, “Nok” (i.e., SPGS-550-M; β-sitosteryl polyoxoethanylsuccinate), soon to be commercially available from Aldrich, can be prepared in two steps using an abundant plant feedstock, β-sitosterol, together with succinic anhydride and PEG-550-M. Upon dissolution in water it forms nanomicelles that serve as nanoreactors, which can be characterized by both cryo-TEM and dynamic light scattering analyses. Several transition metal-catalyzed reactions have been run under micellar conditions to evaluate this surfactant relative to results obtained in nanoparticles composed of TPGS-750-M (i.e., a second generation surfactant). It is shown that Nok usually affords yields that are, in general, as good or better than those typically obtained with TPGS-750-M, and yet is far less costly.

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.63–7.56 (d, J = 16.1 Hz, 1H), 7.55–7.49 (m, 2H), 7.42–7.34 (m, 3H), 6.41–6.35 (d, J = 16.1 Hz, 1H), 1.55 (s, 9H). 39 …”

Section: Methodsmentioning

confidence: 99%

“Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature

2014

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“…(8) Some recent developments involve oxygen and base-free reactions without external oxidant(9) and the identification of new nonphenanthroline type ligands. (10)…”

Section: Introductionmentioning

confidence: 99%

“…The use of acrolein in an oxidative Heck is limited,(18) but the palladium(II)-catalyzed Heck coupling of the related methyl vinyl ketone with various boronic acids has been reported with yields between 50% and 88%. 4,8,10,31 …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Cinnamaldehyde Derivatives by an Oxidative Heck Reaction and Their Use as Starting Materials for Preparation of Mycobacterium tuberculosis 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase Inhibitors

et al. 2011

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Cinnamaldehyde derivatives were synthesized in good to excellent yields in one step by a mild and selective, base-free palladium(II)-catalyzed oxidative Heck reaction starting from acrolein and various arylboronic acids. Prepared α,β-unsaturated aldehydes were used for synthesis of novel α-aryl substituted fosmidomycin analogues, which were evaluated for their inhibition of Mycobacterium tuberculosis 1-deoxy-d-xylulose 5-phosphate reductoisomerase. IC50 values between 0.8 and 27.3 μM were measured. The best compound showed activity comparable to that of the most potent previously reported α-aryl substituted fosmidomycin-class inhibitor.

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“…Although many previous studies focused on oxidative Heck reactions of activated alkenes such as cyclohexenones[16] and acrylate esters,[15] several recent studies have reported high yields and in several cases excellent regioselectivities in oxidative Heck reactions of isolated alkenes. [17–19] This sets the stage for development of this reaction into a protein ligation strategy for isolated alkene systems.…”

mentioning

confidence: 99%

“…We had developed BIAN earlier as a superior ligand for oxidative Heck reactions of challenging substrates. [16] Using mass spectrometry we demonstrated selective and complete ligation of a fluorescently labeled phenylboronic acid derivative to protein-bound alkenes, even in the presence of complex protein mixtures from cell lysates.…”

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confidence: 99%

Aqueous Oxidative Heck Reaction as a Protein‐Labeling Strategy

et al. 2013

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An increasing number of chemical reactions are being employed for bio-orthogonal ligation of detection labels to protein-bound functional groups. Several of these strategies, however, are limited in their application to pure proteins and are ineffective in complex biological samples such as cell lysates. Here we present the palladium-catalyzed oxidative Heck reaction as a new and robust bio-orthogonal strategy for linking functionalized arylboronic acids to protein-bound alkenes in high yields and with excellent chemoselectivity even in the presence of complex protein mixtures from living cells. Advantageously, this reaction proceeds under aerobic conditions, whereas most other metal-catalyzed reactions require inert atmosphere.

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Pd-Diimine: A Highly Selective Catalyst System for the Base-Free Oxidative Heck Reaction

Abstract: Pd(OAc)(2)/3 is an efficient catalyst system for the base-free oxidative Heck reaction that outperforms the currently available catalysts for the more challenging substrates studied. The catalyst system is highly selective, and works at room temperature with dioxygen as the oxidant.

Cited by 88 publications

References 28 publications

“Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature

“Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature

Synthesis of Functionalized Cinnamaldehyde Derivatives by an Oxidative Heck Reaction and Their Use as Starting Materials for Preparation of Mycobacterium tuberculosis 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase Inhibitors

Aqueous Oxidative Heck Reaction as a Protein‐Labeling Strategy

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