Novel methodologies for the synthesis of functionalized lipophilic carboranes

Jonnalagadda, Subash C.; Verga, S.; Patel, Parimal; Reddy, A. Venugopal; Srinivas, T.; Scott, Patricia M.; Mereddy, Venkatram R.

doi:10.1002/aoc.1598

Cited by 8 publications

(1 citation statement)

References 26 publications

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“…Carboranyl aldehydes have been exploited as valuable synthons for the synthesis of diversely decorated carboranes for material and biomedical applications . Considering their functional diversity and facile accessibility, carboranyl aldehydes may be competent functional substrates for cage B–H functionalization. However, in contrast to the superior directing power of carboxylic acids, the carbonyl groups in aldehydes or ketones are less coordinative.…”

Section: Introductionmentioning

confidence: 99%

Selective Catalytic B–H Arylation of o-Carboranyl Aldehydes by a Transient Directing Strategy

et al. 2017

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Carboranyl aldehydes are among the most useful synthons in derivatization of carboranes. However, compared to the utilization of carboranyl carboxylic acids in selective B-H bond functionalizations, the synthetic application of carboranyl aldehydes is limited due to the weakly coordinating nature of the aldehyde group. Herein, the direct arylation of o-carboranyl aldehydes has been developed via Pd-catalyzed cage B-H bond functionalization. With the help of glycine to generate a directing group (DG) in situ, a series of cage B(4,5)-diarylated- and B(4)-monoarylated-o-carboranyl aldehydes were obtained in good to excellent yields with high selectivity. A wide range of functional groups are tolerated. The aldehyde group in the B-H arylated products could be readily removed or transformed into o-carboranyl methanol. A plausible catalytic cycle for B-H arylation was proposed based on control experiments and stoichiometric reactions, including the isolation of a key bicyclic palladium complex.

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Section: Introductionmentioning

confidence: 99%

Selective Catalytic B–H Arylation of o-Carboranyl Aldehydes by a Transient Directing Strategy

et al. 2017

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Boron‐Containing Lipids and Liposomes: New Conjugates of Cholesterol with Polyhedral Boron Hydrides

Bregadze

Sivaev

Dubey

et al. 2020

Chemistry A European J

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As eries of boron-containing lipids werep repared by reactions of cyclic oxonium derivatives of polyhedron boranesa nd metallacarboranes (closo-dodecaborate anion, cobalt and iron bis(dicarbollides)) with amine and carboxylic acids which are derived from cholesterol. Stable liposomal formulations,o nt he basis of synthesized boron-containing lipids, hydrogenated soybean l-a-phosphatidylcholinea nd (HSPC) 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (DSPE-PEG) as excipients,w ere prepared and then characterizedb yd ynamic light scattering(DLS) that revealed the formation of particles to be smaller than 200 nm in diameter.T he resulting liposomal formulationss howed moderate to excellent loading and entrapmente fficiency, thus justifying the design of the compounds to fit in the lipid bilayer and ensuringease of in vivo use for futurea pplication. The liposomalf ormulations based on cobalt and iron bis(dicarbollide)-based lipids were found to be nontoxic against both human breast normale pithelial cells MCF-10A and human breast cancer cells MCF-7.

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Carboranes in Medicine

Grimes

2016

Carboranes

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Novel methodologies for the synthesis of functionalized lipophilic carboranes

Cited by 8 publications

References 26 publications

Selective Catalytic B–H Arylation of o-Carboranyl Aldehydes by a Transient Directing Strategy

Selective Catalytic B–H Arylation of o-Carboranyl Aldehydes by a Transient Directing Strategy

Boron‐Containing Lipids and Liposomes: New Conjugates of Cholesterol with Polyhedral Boron Hydrides

Carboranes in Medicine

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