Cavitands with inwardly and outwardly directed functional groups

Kanaura, Mao; Ito, Kouhei; Schramm, Michael; Ajami, Dariush; Iwasawa, Tetsuo

doi:10.1016/j.tetlet.2015.06.072

Cited by 5 publications

(3 citation statements)

References 39 publications

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“…The synthesis of 2 started from the versatile hexaamido-diol cavitand 3 (Scheme ). After some experimentation, we found that condensation of 3 with meta-substituted dibromomethylpyridine 4 proceeded cleanly and in good yield . Pyridine building block 4 was prepared in 3 steps from commercially available 2-bromo-5-methylpyridine (see SI).…”

Section: Resultsmentioning

confidence: 84%

“…14 After some experimentation, we found that condensation of 3 with meta substituted dibromomethyl pyridine 4 proceeded cleanly and in good yield. 15 Pyridine building block 4 was prepared in 3 steps from commercially available 2-bromo-5-methylpyridine (see SI). Mesylation of hydroxyl derivative 5 with mesyl chloride proceeded with concomitant substitution by chloride to deliver key intermediate 6, which was univocally characterized by X-ray crystallography.…”

Section: Resultsmentioning

confidence: 99%

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A Deep Cavitand Receptor Functionalized with Fe(II) and Mn(II) Aminopyridine Complexes for Bioinspired Oxidation Catalysis

2018

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A deep cavitand receptor 2 based on a resorcinarene scaffold and functionalized with a bis(pyridyl)dipyrrolidine tetradentate ligand has been obtained. Binding of divalent metal ions (M 2+ = Mn 2+ , Fe 2+ and Zn 2+) at the tetradentate ligand results in the formation of cavitand complexes 2•M(OTf) 2. The complexes exhibit selective binding of alkylammonium ions and amides within the cavitand. 2•M(OTf) 2 (M = Fe(II) and Mn(II)) catalyze selective hydroxylation of aliphatic C-H bonds and epoxidation of olefins with hydrogen peroxide, exhibiting selectivity patterns consistent with the implication of high valent metal-oxo species. Furthermore, 2•Fe(OTf) 2 reacts with IO 4 to form an oxoiron(IV) complex [2•Fe(O)] 2+ , without decomposition of the supramolecular container. This species is relatively stable at 0 °C, yet engages in fast oxygen atom transfer reactions.

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Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 99%

A Deep Cavitand Receptor Functionalized with Fe(II) and Mn(II) Aminopyridine Complexes for Bioinspired Oxidation Catalysis

2018

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“…[17] The introverted allyl cavitand enabled us to realize that it has higher reactivity than the extroverted one toward meta-chloroperoxybenzoic acid (mCPBA). Such a supramolecular effect drove us to develop a new pyridine N-oxide cavitand as a supporting ligand in transition metal catalyzed reactions, [18] but N-oxide was unsuccessful in a variety of otherwise straightforward catalytic transformations. We thus have focused our attention on supramolecular frameworks that would support an inwardly located metal center for improving chemical transformations.…”

Section: Introductionmentioning

confidence: 99%