Synthesis of borasiloxane-based macrocycles by multicomponent condensation reactions in solution or in a ball mill

Pascu, Mirela; Ruggi, Albert; Scopelliti, Rosario; Severin, Kay

doi:10.1039/c2cc37538a

Cited by 82 publications

(42 citation statements)

References 40 publications

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“…Ball milling of the boronic acid, the silane diol, and the diamine gave higher yields (85 %). The mechanochemical syntheses of borasiloxanemacrocycles appear to be superior to solution methods in terms of yields 79…”

Section: Omcs From Multiple Bondsmentioning

confidence: 99%

Stimuli‐Responsive Polymeric Nanoparticles for Nanomedicine

Crucho

2014

ChemMedChem

147

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Nature continues to be the ultimate in nanotechnology, where polymeric nanometer-scale architectures play a central role in biological systems. Inspired by the way nature forms functional supramolecular assemblies, researchers are trying to make nanostructures and to incorporate these into macrostructures as nature does. Recent advances and progress in nanoscience have demonstrated the great potential that nanomaterials have for applications in healthcare. In the realm of drug delivery, nanomaterials have been used in vivo to protect the drug entity in the systemic circulation, ensuring reproducible absorption of bioactive molecules that do not naturally penetrate biological barriers, restricting drug access to specific target sites. Several building blocks have been used in the formulation of nanoparticles. Thus, stability, drug release, and targeting can be tailored by surface modification. Herein the state of the art of stimuli-responsive polymeric nanoparticles are reviewed. Such systems are able to control drug release by reacting to naturally occurring or external applied stimuli. Special attention is paid to the design and nanoparticle formulation of these so-called smart drug-delivery systems. Future strategies for further developments of a promising controlled drug delivery responsive system are also outlined.

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Section: Omcs From Multiple Bondsmentioning

confidence: 99%

Stimuli‐Responsive Polymeric Nanoparticles for Nanomedicine

Crucho

2014

ChemMedChem

147

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“…Borasiloxanes, which contain [B‐O‐Si] sequences, can be used to produce borosilicates, heat and chemical resistant polymers, and polymer sensors . Traditional synthetic routes typically involve the condensation of various boron‐ and silicon‐based reagents, but suffer from low atom‐efficiency and selectivity, and commonly entail the release of toxic or corrosive waste . Prior to our communication, a handful of catalysed processes relying on late‐transition‐metal complexes, Sc(OTf) 3 or Mo(CO) 6 had been shown to yield borasiloxanes upon coupling of silanols or hydrosilanes with hydroboranes, diboranes, boraxanes, allylborane or vinylboronates.…”

Section: Introductionmentioning

confidence: 99%

Barium‐Catalysed Dehydrocoupling of Hydrosilanes and Borinic Acids: A Mechanistic Insight

Coz

Zhang

Roisnel

et al. 2020

Chemistry A European J

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Two very rare cases of barium boryloxides, the homoleptic [Ba(OB{CH(SiMe3)2}2)2⋅C7H8] and the heteroleptic [{LONO4}BaOB{CH(SiMe3)2}2] stabilised by the multidentate aminoetherphenolate {LONO4}−, are presented, and their structural properties are discussed. The electron‐deficient [Ba(OB{CH(SiMe3)2}2)2⋅C7H8] shows, in particular, resilient η6‐coordination of the toluene molecule. Together with its amido parents [Ba{N(SiMe3)2}2⋅thf2] and [Ba{N(SiMe3)2}2]2, this complex catalyses the fast and chemoselective dehydrocoupling of borinic acids R2BOH and hydrosilanes HSiR′3, yielding borasiloxanes R2BOSiR′3 in a controlled fashion. The assessment of substrate scope indicates that, for now, the reaction is limited to bulky borinic acids. Kinetic analysis shows that the rate‐limiting step of the catalytic manifold traverses a dinuclear transition state. A detailed mechanistic scenario is proposed on the basis of DFT computations, the results of which are fully consistent with experimental data. It consists of a stepwise process with rate‐determining nucleophilic attack of a metal‐bound O‐atom onto the incoming hydrosilane, involving throughout dinuclear catalytically active species.

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“…53 Here, first the condensation of silane diols with boronic acids gave the cyclic borosiloxanes, and subsequent combination with the diamines produced the corresponding borosiloxane-based macrocycles.…”

Section: Macrocycle Formationmentioning

confidence: 99%

CHAPTER 1. Carbon–Heteroatom Bond Forming Reactions and Heterocycle Synthesis under Ball Milling

Ranu¹,

Chatterjee²,

Mukherjee³

2014

Green Chemistry Series

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Synthesis of borasiloxane-based macrocycles by multicomponent condensation reactions in solution or in a ball mill

Abstract: Large macrocycles containing imine and borasiloxane links are obtained in polycondensation reactions of 4-formylbenzeneboronic acid, t-Bu(2)Si(OH)(2), and diamines. The multicomponent reactions can be performed in solution or--advantageously--by mechanochemical syntheses in a ball mill.

Cited by 82 publications

References 40 publications

Stimuli‐Responsive Polymeric Nanoparticles for Nanomedicine

Stimuli‐Responsive Polymeric Nanoparticles for Nanomedicine

Barium‐Catalysed Dehydrocoupling of Hydrosilanes and Borinic Acids: A Mechanistic Insight

CHAPTER 1. Carbon–Heteroatom Bond Forming Reactions and Heterocycle Synthesis under Ball Milling

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