Transition Metal‐Free Regio‐ and Stereo‐Selective trans Hydroboration of 1,3‐Diynes: A Phosphine‐Catalyzed Access to (E)‐1‐Boryl‐1,3‐Enynes

Please always quote using this URN: urn:nbn:de:bvb:20-opus-293784
  • We report a transition metal‐free, regio‐ and stereo‐selective, phosphine‐catalyzed method for the trans hydroboration of 1,3‐diynes with pinacolborane that affords (E)‐1‐boryl‐1,3‐enynes. The reaction proceeds with excellent selectivity for boron addition to the external carbon of the 1,3‐diyne framework as unambiguously established by NMR and X‐ray crystallographic studies. The reaction displays a broad substrate scope including unsymmetrical diynes to generate products in high yield (up to 95 %). Experimental and theoretical studies suggestWe report a transition metal‐free, regio‐ and stereo‐selective, phosphine‐catalyzed method for the trans hydroboration of 1,3‐diynes with pinacolborane that affords (E)‐1‐boryl‐1,3‐enynes. The reaction proceeds with excellent selectivity for boron addition to the external carbon of the 1,3‐diyne framework as unambiguously established by NMR and X‐ray crystallographic studies. The reaction displays a broad substrate scope including unsymmetrical diynes to generate products in high yield (up to 95 %). Experimental and theoretical studies suggest that phosphine attack on the alkyne is a key process in the catalytic cycle.show moreshow less

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Metadaten
Author: Swetha Jos, Connor Szwetkowski, Carla Slebodnick, Robert Ricker, Ka Lok Chan, Wing Chun Chan, Udo Radius, Zhenyang Lin, Todd B. Marder, Webster L. Santos
URN:urn:nbn:de:bvb:20-opus-293784
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Language:English
Parent Title (English):Chemistry – A European Journal
Year of Completion:2022
Volume:28
Issue:63
Article Number:e202202349
Source:Chemistry – A European Journal 2022, 28(63):e202202349. DOI: 10.1002/chem.202202349
DOI:https://doi.org/10.1002/chem.202202349
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:enediyne; enyne; hydroboration; organocatalytic; stereoselective
Release Date:2023/06/19
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International