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      Synthesis of 1,3-Enynes by Iron-Catalyzed Propargylic C–H Functionalization: An Alkyne Analogue for the Eschenmoser Methenylation

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          Abstract

          A two-step protocol for the conversion of alkyl-substituted alkynes to 1,3-enynes is reported. In this α-methenylation process, an iron-catalyzed propargylic C–H functionalization delivers tetramethylpiperidine-derived homopropargylic amines which undergo facile Cope elimination upon N-oxidation to afford the enyne products. A range of aryl alkyl and dialkyl acetylenes were found to be suitable substrates for this process, which constitutes an alkyne analogue for the Eschenmoser methenylation of carbonyl derivatives. In addition, a new bench-stable precatalyst for iron-catalyzed propargylic C–H functionalization is reported.

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          Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives.

          S Saito, Y. Yamamoto (2000)
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            Palladium-Based Catalytic Systems for the Synthesis of Conjugated Enynes by Sonogashira Reactions and Related Alkynylations

            Henri Doucet, Jean-Cyrille Hierso (2007)
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              Diastereo- and Enantioselective Reactions of Bis(pinacolato)diboron, 1,3-Enynes, and Aldehydes Catalyzed by an Easily Accessible Bisphosphine–Cu Complex

              Fanke Meng, Fredrik Haeffner, Amir H. Hoveyda (2014)
              Catalytic enantioselective multicomponent processes involving bis(pinacolato)diboron [B2(pin)2], 1,3-enynes, and aldehydes are disclosed; the resulting compounds contain a primary C–B(pin) bond, as well as alkyne- and hydroxyl-substituted tertiary carbon stereogenic centers. A critical feature is the initial enantioselective Cu–B(pin) addition to an alkyne-substituted terminal alkene. This and other key mechanistic issues have been investigated by DFT calculations. Reactions are promoted by the Cu complex of a commercially available enantiomerically pure bis-phosphine and are complete in 8 h at ambient temperature; products are generated in 66–94% yield (after oxidation or catalytic cross-coupling), 90:10 to >98:2 diastereomeric ratio, and 85:15–99:1 enantiomeric ratio. Aryl-, heteroaryl-, alkenyl-, and alkyl-substituted aldehydes and enynes can be used. Utility is illustrated through catalytic alkylation and arylation of the organoboron products as well as applications to synthesis of fragments of tylonolide and mycinolide IV.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Org Lett
                Journal ID (iso-abbrev): Org Lett
                Journal ID (publisher-id): ol
                Journal ID (coden): orlef7
                Title: Organic Letters
                Publisher: American Chemical Society
                ISSN (Print): 1523-7060
                ISSN (Electronic): 1523-7052
                Publication date (Electronic): 11 April 2024
                Publication date Collection: 26 April 2024
                Volume: 26
                Issue: 16
                Pages: 3355-3360
                Affiliations
                [† ]Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States
                [‡ ]School of Chemistry & Chemical Engineering, Yangzhou University , Yangzhou, Jiangsu 225002, China
                Author notes
                Author information
                https://orcid.org/0000-0001-9560-3186
                https://orcid.org/0000-0001-6414-0908
                Article
                DOI: 10.1021/acs.orglett.4c00696
                PMC ID: 11059102
                PubMed ID: 38604973
                SO-VID: 560a755d-a195-4b5b-8d80-0c2f7895f3e9
                Copyright © © 2024 The Authors. Published by American Chemical Society
                License:

                Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained ( https://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 27 February 2024
                Date accepted : 09 April 2024
                Date revision received : 08 April 2024
                Funding
                Funded by: National Institute of General Medical Sciences, doi 10.13039/100000057;
                Award ID: R35GM142945
                Categories
                Subject: Letter
                Custom metadata
                document-id-old-9 ol4c00696
                document-id-new-14 ol4c00696
                ccc-price

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry

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