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      Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs

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          Summary

          The formation of alkylidenezinc carbenoids by 1,4-addition/carbozincation of dialkylzincs or alkyl iodides based on zinc atom radical transfer, in the presence of dimethylzinc with β-(propargyloxy)enoates having pendant iodo- and bromoalkynes, is disclosed. Formation of the carbenoid intermediate is fully stereoselective at −30 °C and arises from a formal anti-selective carbozincation reaction. Upon warming, the zinc carbenoid is stereochemically labile and isomerizes to its more stable form.

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          Carbometallation (C-Metallation) of Alkynes: Stereospecific Synthesis of Alkenyl Derivatives

          Jean F. Normant, Alexandre Alexakis (1981)
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            Addition of metal enolate derivatives to unactivated carbon-carbon multiple bonds.

            F Toumelin-Chemla, Fabrice Dénès, Alejandro Lopez-Perez (2010)
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              Metal-Catalyzed Cross-Couplig Reactions

              A. Meijere, F. DIEDERICH, F. Diederich … (2004)
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                Author and article information

                Contributors
                Fabrice Chemla
                Alejandro Pérez-Luna
                Ilan Marek: Role: Guest Editor
                Journal
                Journal ID (nlm-ta): Beilstein J Org Chem
                Journal ID (iso-abbrev): Beilstein J Org Chem
                Title: Beilstein Journal of Organic Chemistry
                Publisher: Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                ISSN (Electronic): 1860-5397
                Publication date Collection: 2013
                Publication date (Electronic): 4 February 2013
                Volume: 9
                Pages: 236-245
                Affiliations
                [1 ]Institut Parisien de Chimie Moléculaire (UMR 7201), FR 2769, UPMC Univ Paris 06, CNRS, Bâtiment F 2ème et., Case 183, 4 place Jussieu, F-75005 Paris, France
                Article
                DOI: 10.3762/bjoc.9.28
                PMC ID: 3566799
                PubMed ID: 23399921
                SO-VID: 2878d209-1575-4c9e-bf6f-ef2fba4e2969
                Copyright © Copyright © 2013, Chemla et al; licensee Beilstein-Institut.
                License:

                This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                History
                Date received : 13 November 2012
                Date accepted : 8 January 2013
                Categories
                Subject: Full Research Paper
                Subject: Chemistry
                Subject: Organic Chemistry

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: carbenoids,carbometallation,carbozincation,radicals,tandem reaction
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: carbenoids, carbometallation, carbozincation, radicals, tandem reaction

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