Iron- and Cobalt-Catalyzed Arylation of Azetidines, Pyrrolidines, and Piperidines with Grignard Reagents

Barré, Baptiste; Gonnard, Laurine; Campagne, Rémy; Reymond, Sébastien; Marin, Julien; Ciapetti, Paola; Brellier, Marie; Guérinot, Amandine; Cossy, Janine

doi:10.1021/ol503043r

Cited by 69 publications

(31 citation statements)

References 45 publications

(16 reference statements)

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“…Recently, the scope of the reaction with the optimized conditions was reported and the N‐protecting‐group tolerance was first examined 21. As mentioned before, the reaction was compatible with an N ‐carbamate.…”

Section: Resultsmentioning

confidence: 94%

“…The N ‐Boc‐4‐iodopiperidine ( 1 a ) was selected for the evaluation of the reactivity of a large variety of aryl magnesium bromides. We had already noticed that the electronic nature of the substituent on the aryl group of the Grignard reagent did not seem to play a significant role in the outcome of the reaction 21. Indeed, electron‐rich aromatic Grignard reagents such as p ‐tolyl‐ and m ‐OMe‐phenylmagnesium bromide were suitable coupling partners and allowed the formation of the corresponding 4‐aryl piperidines 2 d and 2 e in excellent yields (81 and 85 %, respectively) (Table 2, entries 1 and 2).…”

Section: Resultsmentioning

confidence: 99%

“…In the course of our studies toward the development of sustainable synthetic methods to access pharmaceutically relevant scaffolds, we recently developed an iron-and cobalt-catalyzed arylationo fs aturated N-heterocycles by using Grignardr eagents. [21] Notably,alarge variety of 4-(hetero)aryl piperidines were preparedt hrough ac obalt-catalyzed cross-coupling. Further studies allowed us to extend the method to the preparation of 4-alkenyl and 4-allyl piperidines.…”

Section: Introductionmentioning

confidence: 99%

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Cobalt‐Catalyzed Cross‐Coupling of 3‐ and 4‐Iodopiperidines with Grignard Reagents

Gonnard

Guérinot

Cossy

2015

Chemistry A European J

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cobalt‐Catalyzed Cross‐Coupling of 3‐ and 4‐Iodopiperidines with Grignard Reagents

Gonnard

Guérinot

Cossy

2015

Chemistry A European J

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“…15 This could allow a rather direct and efficient access to a broad range of 2,3-disubstituted azetidines, 16 and other pharmaceutically relevant nitrogen heterocycles.…”

Section: Figure 1 Examples Of Biologically Active 3-oxygenated Azetimentioning

confidence: 99%

“…15 This could allow a rather direct and efficient access to a broad range of 2,3-disubstituted azetidines, 16 and other pharmaceutically relevant nitrogen heterocycles. 17 Our proposed strategy from commercial N-Boc-azetidin-3-one is depicted in Scheme 1.…”

Section: Figure 1 Examples Of Biologically Active 3-oxygenated Azetimentioning

confidence: 99%

Asymmetric Synthesis of 2-Substituted Azetidin-3-ones via Metalated SAMP/RAMP Hydrazones

et al. 2016

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Permanent WRAP URL:http://wrap.warwick.ac.uk/79725 Copyright and reuse:The Warwick Research Archive Portal (WRAP) makes this work by researchers of the University of Warwick available open access under the following conditions. Copyright © and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable the material made available in WRAP has been checked for eligibility before being made available.Copies of full items can be used for personal research or study, educational, or not-for profit purposes without prior permission or charge. Provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. Publisher's statement:"This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Journal of Organic Chemistry copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work http://pubs.acs.org/page/policy/articlesonrequest/index.html ." A note on versions:The version presented here may differ from the published version or, version of record, if you wish to cite this item you are advised to consult the publisher's version. Please see the 'permanent WRAP url' above for details on accessing the published version and note that access may require a subscription. Just Accepted "Just Accepted" manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides "Just Accepted" as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. "Just Accepted" manuscripts appear in full in PDF format accompanied by an HTML abstract. "Just Accepted" manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). "Just Accepted" is an optional service offered to authors. Therefore, the "Just Accepted" Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the "Just Accepted" Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these "Just Accepted" manuscripts. Asymmetric Synthesis of 2-Substituted Azetidin-3-ones via Metalated SAMP/RAMP Hydrazones TABLE OF CONTENTS/ABSTRACT:2-Substituted azetidin-3-ones can be prepared in good yields and enantioselectivities ...

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Discussion Addendum for: 4‐Nonylbenzoic Acid

Fürstner¹

2020

Organic Syntheses

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This addendum presents various examples that illustrate the tremendous advances in the iron‐catalyzed cross coupling since the original Organic Syntheses procedure was published in 2005. The 2005 Organic Syntheses procedures describing the preparation of 4‐nonylbenzoic acid, a component of liquid crystalline materials, captures the state of development of iron catalysis. It is pointed out that alkyl/aryl cross coupling can be effected without preparing a Grignard reagent in a separate step. The promise that cheap and benign iron catalysts allow palladium to be substituted – at least in certain cross coupling reactions – was a major incentive. It soon became clear that this metal is also able to promote cross coupling reactions of substrates that have little or no precedent in the classical canon.

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Iron- and Cobalt-Catalyzed Arylation of Azetidines, Pyrrolidines, and Piperidines with Grignard Reagents

Abstract: Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.

Cited by 69 publications

References 45 publications

Cobalt‐Catalyzed Cross‐Coupling of 3‐ and 4‐Iodopiperidines with Grignard Reagents

Cobalt‐Catalyzed Cross‐Coupling of 3‐ and 4‐Iodopiperidines with Grignard Reagents

Asymmetric Synthesis of 2-Substituted Azetidin-3-ones via Metalated SAMP/RAMP Hydrazones

Discussion Addendum for: 4‐Nonylbenzoic Acid

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