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Synthesis of arylidene-β-lactams via exo-selective matsuda-heck arylation of methylene-β-lactams
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Riemer, Nastja, Riemer, Martin, Krüger, Mandy , Clarkson, Guy J., Shipman, Michael and Schmidt, Bernd (2021) Synthesis of arylidene-β-lactams via exo-selective matsuda-heck arylation of methylene-β-lactams. The Journal of Organic Chemistry, 86 (13). pp. 8786-8796. doi:10.1021/acs.joc.1c00638 ISSN 0022-3263.
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WRAP-Synthesis-arylidene-β-lactams via exo-selective matsuda-2021.pdf - Accepted Version - Requires a PDF viewer. Download (1306Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.joc.1c00638
Abstract
exo-Methylene-β-lactams were synthesized in two steps from commercially available 3-bromo-2-(bromomethyl)propionic acid and reacted with arene diazonium salts in a Heck-type arylation in the presence of catalytic amounts of Pd(OAc)2 under ligand-free conditions. The products, arylidene-β-lactams, were obtained in high yields as single isomers. The β-hydride elimination step of the Pd-catalyzed coupling reaction proceeds with high exo-regioselectivity and E-stereoselectivity. With aryl iodides, triflates, or bromides, the coupling products were isolated only in low yields, due to extensive decomposition of the starting material at elevated temperatures. This underlines that arene diazonium salts can be superior arylating reagents in Heck-type reactions and yield coupling products in synthetically useful yields and selectivities when conventional conditions fail.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
Library of Congress Subject Headings (LCSH): | Lactams -- Synthesis, Arylation, Salts, Hydrocarbons, Nuclear magnetic resonance spectroscopy | ||||||||
Journal or Publication Title: | The Journal of Organic Chemistry | ||||||||
Publisher: | American Chemical Society | ||||||||
ISSN: | 0022-3263 | ||||||||
Official Date: | 2 July 2021 | ||||||||
Dates: |
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Volume: | 86 | ||||||||
Number: | 13 | ||||||||
Page Range: | pp. 8786-8796 | ||||||||
DOI: | 10.1021/acs.joc.1c00638 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Reuse Statement (publisher, data, author rights): | “This document is the Accepted Manuscript version of a Published Work that appeared in final form in The 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 see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].” | ||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||
Date of first compliant deposit: | 16 June 2021 | ||||||||
Date of first compliant Open Access: | 22 June 2022 | ||||||||
RIOXX Funder/Project Grant: |
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