Bismuth(iii) triflate promoted intramolecular hydroamination of unactivated alkenyl sulfonamides in the preparation of pyrrolidines

Mathia, František; Szolcsányi, Peter

doi:10.1039/c2ob07064b

Cited by 27 publications

(3 citation statements)

References 77 publications

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“…A procedure for intramolecular catalytic hydroamination of unactivated alkenyl sulfonamides under mild conditions was developed, to access saturated nitrogen‐containing heterocycles . Several metal‐based catalysts provided the expected N ‐protected methylpyrrolidines but with slower reaction rates than bismuth(III) triflate (Scheme ).…”

Section: Olefin Activationmentioning

confidence: 99%

Cyclisations Catalysed by Bismuth(III) Triflate

2016

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Cyclisation reactions have always drawn the attention of organic chemists in pursuit of methods for the selective construction of natural‐product‐like polycyclic compounds. The search for new and efficient ring‐forming reactions has witnessed growing interest, resulting in the design of many elegant synthetic strategies and the discovery of useful methodologies. In this context, cycloisomerisation reactions are very attractive, because they allow for the rapid generation of molecular complexity with use of a low loading of a promoter, thus limiting waste production. The search for sustainable and more efficient catalytic systems remains challenging. Relatively nontoxic and inexpensive bismuth(III) salts are of particular interest for catalytic organic synthesis. More specifically, the highly active triflate salt is known to be noncorrosive and easy to handle. This microreview focuses on cyclisation reactions assisted by bismuth(III) triflate catalysis.

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Section: Olefin Activationmentioning

confidence: 99%

Cyclisations Catalysed by Bismuth(III) Triflate

2016

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“…To further support this claim, we investigated the reaction mechanism of another organic transformation catalyzed by Bi(OTf) 3 i. e. hydroamination of an unactivated alkenyl sulphonamide (transformation 17 → 18 , Figure 6). [9] This reaction was proposed by Mathia and Szolcsányi to occur via a Bi‐assisted Brønsted acid activation mode [8,9] . Figure 6 shows the results of our calculations regarding the mechanism of this transformation.…”

Section: Resultsmentioning

confidence: 74%

How a Bismuth(III) Catalyst Achieves Greatest Activation of Organic Lewis Bases in a Catalytic Reaction: Insights from DFT Calculations

et al. 2020

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Density functional theory (DFT) was utilized to understand how bismuth(III) salts (BiX3) achieve greatest activation of organic Lewis bases in a catalytic reaction. It is reported in the literature that the BiX3 reactivity originates from its low lying Bi−X σ* orbital. In contrast to this belief, we will show here that for BiX3 to effectively serve as a catalyst, a p orbital of bismuth needs to be involved in activating organic substrates.

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“…A catalytic intramolecular hydroamination of unactivated alkenyl sulfonamides was developed using Bi(OTf ) 3 . 15 The reaction proceeds under simple conditions and provides an easy access to 2-methylpyrrolidines in high yields (Scheme 10). Control experiments supported the hypothesis that the actual hydroamination catalyst might be HOTf generated from Bi(OTf ) 3 .…”

Section: Hydroamination Reaction Of Alkenyl Sulfonamidesmentioning

confidence: 99%

New trends in bismuth-catalyzed synthetic transformations

Ollevier

2013

Org. Biomol. Chem.

207

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This review covers uses of bismuth catalysts since 2005 with a special emphasis on the emerging applications of such catalysts. Low toxicity, low catalytic loading, synergistic effects with other catalysts, and some hydrocompatibility properties confer to bismuth salts major advantages. The expanding activity in the field clearly highlights the growing potential of bismuth catalysts. The article is not a comprehensive review on bismuth catalysis but a selection of its most promising uses in challenging synthetic transformations.

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Bismuth(iii) triflate promoted intramolecular hydroamination of unactivated alkenyl sulfonamides in the preparation of pyrrolidines

Cited by 27 publications

References 77 publications

Cyclisations Catalysed by Bismuth(III) Triflate

Cyclisations Catalysed by Bismuth(III) Triflate

How a Bismuth(III) Catalyst Achieves Greatest Activation of Organic Lewis Bases in a Catalytic Reaction: Insights from DFT Calculations

New trends in bismuth-catalyzed synthetic transformations

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