Practical and regioselective amination of arenes using alkyl amines

Ruffoni, Alessandro; Juliá, Fabio; Svejstrup, Thomas D.; McMillan, Alastair J.; Douglas, James J.; Leonori, Daniele

doi:10.1038/s41557-019-0254-5

Cited by 211 publications

(151 citation statements)

References 50 publications

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“…The reduction of primary amides to primary amines is more stringent compared to secondary and tertiary amides. 8 Among various synthetic methods to prepare primary amines such as reductive amination of carbonyls, [9][10][11][12][13][14][15] borrowing hydrogenation methodologies, [16][17][18] hydroamination of alkynes, 19,20 reduction of nitriles, [21][22][23][24] primary amides, 25 and carboxylic acids in the presence of ammonia, 26 reduction of primary amides is a straightforward route as amides are stable, naturally abundant, and inexpensive. Common methods for reduction of primary amides employing stoichiometric amounts of reactive metal hydride reagents such as lithium aluminum hydride or sodium borohydrides are unattractive in terms of atom economy and environmental issues.…”

Section: Introductionmentioning

confidence: 99%

Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: integrating nucleophilicity with Lewis acidic activation

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: integrating nucleophilicity with Lewis acidic activation

et al. 2020

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“…fluorobenzene, and improves selectivity towards the para-position. The method was adapted to flow in collaboration with AstraZeneca with piperidine and iodobenzene as reacting partners to furnish the para-substituted building block 1-(4-iodophenyl)piperidine in a productivity of 3.8 g h −1 (Scheme 65) [212]. A different photochemical approach was followed by Marsden and co-workers, performing an intramolecular C − H amination in a mixture of acetic acid and sulfuric acid and fragmenting the protonated Nchloroamine homolytically using UV light [213].…”

Section: − N Bond Formationmentioning

confidence: 99%

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

2020

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C-H functionalization chemistry is one of the most vibrant research areas within synthetic organic chemistry. While most researchers focus on the development of small-scale batch-type transformations, more recently such transformations have been carried out in flow reactors to explore new chemical space, to boost reactivity or to enable scalability of this important reaction class. Herein, an up-to-date overview of C-H bond functionalization reactions carried out in continuous-flow microreactors is presented. A comprehensive overview of reactions which establish the formal conversion of a C-H bond into carbon-carbon or carbonheteroatom bonds is provided; this includes metal-assisted C-H bond cleavages, hydrogen atom transfer reactions and C-H bond functionalizations which involve an S E-type process to aromatic or olefinic systems. Particular focus is devoted to showcase the advantages of flow processing to enhance C-H bond functionalization chemistry. Consequently, it is our hope that this review will serve as a guide to inspire researchers to push the boundaries of C-H functionalization chemistry using flow technology.

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“…piperidines) . In addition to this method, Leonori and co‐workers recently contributed another procedure for the direct amination of arenes starting from simple, unfunctionalized secondary amines …”

Section: C–n Bondmentioning

confidence: 99%

A Retrosynthetic Approach for Photocatalysis

et al. 2020

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Visible‐light‐mediated chemical reactions have become very popular within the last 15 years. Many excellent reviews have summarized reaction principles and recent results in photochemistry and photocatalysis. However, despite their popularity photochemistry and photoredox catalysis are not regular parts of the bachelor and master curriculum of chemistry education. As a consequence, most chemists will use in synthesis planning classic retrosynthetic disconnections and only rarely consider photocatalytic steps. The aim of this article is to be a useful tool for synthetic chemists, that are interested in the synthetic aspects of photocatalysis and looking for a specific retrosynthetic disconnection. Not only are informative schemes provided but also are the availability of the catalysts and reagents as well as the functional group tolerance of the respective method briefly discussed.

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Practical and regioselective amination of arenes using alkyl amines

Cited by 211 publications

References 50 publications

Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: integrating nucleophilicity with Lewis acidic activation

Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: integrating nucleophilicity with Lewis acidic activation

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

A Retrosynthetic Approach for Photocatalysis

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