Synthesis of Mono-<i>O</i>-alkylated Homooxacalix[3]arene and a Protection–Deprotection Strategy for Homooxacalix[3]arene

Wu, Chong; Ikejiri, Yusuke; Zeng, Xi; Elsegood, Mark R. J.; Redshaw, Carl; Yamato, Takehiko

doi:10.1021/acs.orglett.6b03338

Cited by 8 publications

(4 citation statements)

References 51 publications

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“…Over the past few decades, the development of artificial receptors for ion recognition, complexation, and transportation has proven to be an important topic in both environmental and supramolecular chemistry [ 1 , 2 , 3 , 4 ]. Given their ready availability, and their unique conformational and cavity-containing structures, together with their versatile molecular recognition properties, calixarenes have attracted a great deal of attention during the past several decades, and, indeed, calixarene chemistry has become an indispensable part of supramolecular science [ 5 , 6 , 7 , 8 , 9 ]. Calix[ n ]arenes can provide useful building blocks for host-guest type receptors by appropriate modification.…”

Section: Introductionmentioning

confidence: 99%

A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions

Jiang

Ikejiri

et al. 2018

Molecules

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A receptor cone-1 based on a hexahomotrioxacalix[3]arene bearing three pyridyl groups was successfully synthesized, which has a C3-symmetric conformation and is capable of binding alkylammonium and metal ions simultaneously in a cooperative fashion. It can bind alkylammonium ions through the π-cavity formed by three aryl rings. This behaviour is consistent with the cone-in/cone-out conformational rearrangement needed to reorganize the cavity for endo-complexation. As a C3-symmetrical pyridyl-substituted calixarene, receptor cone-1 can also bind an Ag+ ion, and the nitrogen atoms are turned towards the inside of the cavity and interact with Ag+. After complexation of tris(2-pyridylamide) derivative receptor cone-1 with Ag+, the original C3-symmetry was retained and higher complexation selectivity for n-BuNH3+ versus t-BuNH3+ was observed. Thus, it is believed that this receptor will have a role to play in the sensing, detection, and recognition of Ag+ and n-BuNH3+ ions.

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Section: Introductionmentioning

confidence: 99%

A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions

Jiang

Ikejiri

et al. 2018

Molecules

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“…A remarkable example of the regioselective synthesis of mono‐ O ‐alkylated homooxacalix[3]arenes via a protection–deprotection strategy was reported by Yamato et al. The two main steps involve first protection of two OH groups of the homooxacalix[3]arene located at the lower rim, then Pd/C‐catalyzed hydrogenolysis of the 9‐anthrylmethyl groups …”

Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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Palladium on charcoal( Pd/C)h as lots of salient merits:( i) it is ac heap andc ommercial source of palladium, (ii)i ts hows efficientc atalytic activity even without ligands,( iii)a saheterogeneous catalyst it is easily recycledm any times by simple filtration,a nd (iv) it is applicablet oag reat number of reactions and substrates,a lthough it is eventually less efficient than homogeneous Pd catalysts containing some sophisticated ligands.T hisr eview recalls the main background ands ummarizes the progress made essentially during the last twelve years in Pd/C-catalyzed organic synthesis since the reviews by Felpins group andSekiin2 006.

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“…Although there is a vast array of excellently working protection–deprotection protocols in use in sophisticated organic syntheses, the rising complexity of targets requires constant exploration in search for new strategies. Furthermore, in-depth understanding of the chemistry behind well-established protocols allows for their effective development, quite often widening the scope of potential applications. − …”

Section: Introductionmentioning

confidence: 99%

Scrabbling around in Synthetic Nuances Managing Sodium Compounds: Bisphenol/Bisnaphthol Synthesis by Hydroxyl Group Masking

et al. 2020

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A unique method of bisphenol/bisnaphthol synthesis is being proposed, serendipitously discovered in the course of the careful analysis of an aminophenol methylation reaction. The insightful exploration of the synthesis of N- or O-methylated species, originating from functionalized phenols obtained by a conventional strategy, provided the opportunity to discover an unexpected reaction pathway yielding various bisphenols. Sodium complexes were found to be crucial intermediates in the synthetic scenario. Their formation, which is usually an imperceptive step, was substantial for the productive outcome of functional group protection. Thorough exploration revealed an essential structural motif of aminophenolate, necessary for the successful outcome of the reaction, and also enabled establishing the limitations of the new method. The work demonstrated that a slight change in the perspective and close inspection of the synthetic nuances can answer the important question concerning what a specific target-oriented synthesis strategy is lacking.

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Synthesis of Mono-O-alkylated Homooxacalix[3]arene and a Protection–Deprotection Strategy for Homooxacalix[3]arene

Cited by 8 publications

References 51 publications

A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions

A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Scrabbling around in Synthetic Nuances Managing Sodium Compounds: Bisphenol/Bisnaphthol Synthesis by Hydroxyl Group Masking

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