ChemInform Abstract: Designer‐Surfactant‐Enabled Cross‐Couplings in Water at Room Temperature

Lipshutz, Bruce H.; Ghorai, Subir

doi:10.1002/chin.201238257

Cited by 27 publications

(43 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5c). On the basis of our previous experience 39 and other literature studies 40 , we proposed a plausible mechanism for this transformation. We hypothesized that under certain conditions, the organometallic reagents generated in situ 41,42 in water could be temporarily stabilized briefly, for example organozinc reagents (Fig.…”

Section: Discussionmentioning

confidence: 62%

The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water

Zhou

2014

Nat Commun

View full text Add to dashboard Cite

Carbon-carbon bond formation is the essence of organic synthesis. One of the most important methods for forming carbon-carbon bonds is the Barbier-Grignard-type reaction, which was discovered over a century ago. However, it is still highly desirable to further improve this process. In this article, we describe a Barbier-Grignard-type direct arylation of aldehydes by using unactivated iodides mediated by zinc and catalysed by rhodium in water. This method bypasses a number of challenges encountered by the conventional BarbierGrignard reaction, such as strict exclusion of moisture and air, protection-deprotection of various acidic hydrogens in the substrates, and so forth. It thereby creates a safer, more convenient and more environmentally benign strategy to access the diarylmethanols and aryl alkyl alcohols, ubiquitous skeletons found in fine chemicals, biologically active molecules and pharmaceuticals. Importantly, the same reaction performed in an organic solvent proceeded sluggishly to give much inferior yields.

show abstract

Section: Discussionmentioning

confidence: 62%

The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water

Zhou

2014

Nat Commun

View full text Add to dashboard Cite

show abstract

“…With an understanding of the mechanism, students were able to comprehend the purpose of adding potassium hydrosulfate to the aqueous phase of the CM reactions. 3 A brief discussion on the commercialization of the olefin metathesis reaction 23 also resonated well with students, as it highlighted the “real world” applications associated with their laboratory experiment.…”

Section: Discussionmentioning

confidence: 83%

“Click” and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles

et al. 2013

Self Cite

View full text Add to dashboard Cite

The two laboratory reactions focus on teaching several concepts associated with green chemistry. Each uses a commercial, nontoxic, and biodegradable surfactant, TPGS-750-M, to promote organic reactions within the lipophilic cores of nanoscale micelles in water. These experiments are based on work by K. Barry Sharpless (an azide–alkyne “click” reaction) and Robert Grubbs (an olefin cross-metathesis reaction); both are suitable for an undergraduate organic laboratory. The copper-catalyzed azide–alkyne [3+2] cycloaddition of benzyl azide and 4-tolylacetylene is very rapid: the triazole product is readily isolated by filtration and is characterized by thin-layer chromatography and melting point analysis. The ruthenium-catalyzed olefin cross-metathesis reaction of benzyl acrylate with 1-hexene is readily monitored by thin-layer chromatography and gas chromatography. The metathesis experiment comparatively evaluates the efficacy of a TPGS-750-M/water medium relative to a traditional reaction performed in dichloromethane (a common solvent used for olefin metathesis).

show abstract

“…Other application of PTS is concerned with micellar catalysis in chemical reactions. This compound allows to perform the reactions in an aqueous medium, without the addition of any organic solvent (Lipshutz and Ghorai, 2008;Lipshutz and Ghorai, 2012).…”

Section: Introductionmentioning

confidence: 99%

PTS micelles for the delivery of hydrophobic methotrexate

Cerqueira

Noro

Moura

et al. 2019

International Journal of Pharmaceutics

View full text Add to dashboard Cite

Polyoxyethanyl-α-tocopheryl sebacate (PTS) is an amphiphilic compound with self-emulsifying properties known to form micelles. In this work, we report the production of PTS micelles for the encapsulation and delivery of a hydrophobic derivative of methotrexate, MTX di-ethylated (MTX-OEt). We optimized the micelles production by testing two different techniques: auxiliary solvent and sonication. Small and homogeneous micelles (≈40 nm) were obtained through the auxiliary solvent method performed at 30°C and using 15 mg/mL of PTS. The produced micelles with the most promising physicochemical properties did not induce cytotoxicity when tested in normal human cells (BJ5ta cells), being considered for the encapsulation of MTX-OEt. This prodrug was achieved by Fisher esterification using ethanol, being isolated in good yield (η = 68%). MTX-OEt was efficiently encapsulated onto the produced micelles which preserved their physicochemical properties. The PTS micelles loaded with MTX-OEt, free MTX-OEt and free unmodified MTX revealed similar biological effect against cancer cells (Caco-2 cells). These results demonstrated that the biological activity of MTX is not altered after modification. The developed PTS micelles revealed a promising intracellular delivery performance with potentiality for cancer therapy.

show abstract

ChemInform Abstract: Designer‐Surfactant‐Enabled Cross‐Couplings in Water at Room Temperature

Abstract: Review: 141 refs.

Cited by 27 publications

References 64 publications

The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water

The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water

“Click” and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles

PTS micelles for the delivery of hydrophobic methotrexate

Contact Info

Product

Resources

About