Supramolecular Catalysis in the Synthesis of Substituted 1 <i>H</i>‐Tetrazoles from Isonitriles by a Self‐Assembled Hexameric Capsule

Giust, Sonia; Sorella, Giorgio La; Sperni, Laura; Fabris, Fabrizio; Strukul, Giorgio; Scarso, Alessandro

doi:10.1002/ajoc.201402229

Cited by 34 publications

(18 citation statements)

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“…Usually this reaction is carried out in rather harsh conditions that often lead to the possible formation of acid-promoted side reactions also due to poor functional group compatibility that overall limits the applicability of this chemical transformation. [63]. )…”

Section: Cyclization Reactionsmentioning

confidence: 98%

“…It is important to note that the combination with another substrate should be much faster than the reaction with water that is always present in the reaction medium because it is important for the self-assembling of the capsule. After seeking for various nucleophiles, Scarso and coworkers disclosed that the reaction between isonitriles and trimethylsilyl azide could be promoted by the capsule, leading to the rapid formation of the corresponding 1H-tetrazoles [63] without observing the formation of formylamide products typical of the hydration reaction.…”

Section: C-heteroatom Bond-forming Reactionsmentioning

confidence: 99%

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Catalysis Within the Self-Assembled Resorcin[4]arene Hexamer

Borsato

Scarso

2016

Organic Nanoreactors

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This chapter was originally published in the book Organic Nanoreactors. The copy attached is provided by Elsevier for the author's benefit and for the benefit of the author's institution, for noncommercial research, and educational use. This includes without limitation use in instruction at your institution, distribution to specific colleagues, and providing a copy to your institution's administrator. All other uses, reproduction and distribution, including without limitation commercial reprints, selling or licensing copies or access, or posting on open internet sites, your personal or institution's website or repository, are prohibited. For exceptions, permission may be sought for such use through Elsevier's

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Section: Cyclization Reactionsmentioning

confidence: 98%

Section: C-heteroatom Bond-forming Reactionsmentioning

confidence: 99%

Catalysis Within the Self-Assembled Resorcin[4]arene Hexamer

Borsato

Scarso

2016

Organic Nanoreactors

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“…Similar considerations can be related to the synthesis of 1H tetrazoles carried out in capsule 2 (Scheme 4) [24]. Table 2 shows the effect of the hexameric capsule in the click reaction using substrate 11a.…”

Section: Catalysis Into Resorcinarene Hexameric Capsulesmentioning

confidence: 61%

Catalysis inside Supramolecular Capsules: Recent Developments

2019

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In the last decades, supramolecular chemists have developed new molecular receptors able to include a wide range of guests. In addition, they have designed synthetic hosts able to form capsules having an internal volume of thousands of Å3. This inner space shows different features from the bulk solution. In particular, this environment has recently been employed to perform chemical reactions, obtaining reaction products different from the “normal” conditions. These supramolecular capsules act as nanoreactors, catalyzing many chemical transformations. This review collects the recent developments (since 2015) in this field, focusing on supramolecular capsules based on resorcinarene hexameric capsules and metal-cage capsules.

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“…The [2+3] cycloaddition of 14 with trimethylsilyl azide was also unaffected by the addition of HCl (Table , entries 7 A and 7 B) . Employing inhibitor 3 in a large excess did not lead to efficient suppression of the cycloaddition (Table , entries 7 C and 7 D), which might indicate that a significant background reaction takes place outside of capsule I .…”

Section: Figurementioning

confidence: 98%