Dialkynyldiboranes(4) and the selectable reactivity of their C–H, CC and B–B bonds
- 1 February 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 57 (21), 2645-2648
- https://doi.org/10.1039/d1cc00265a
Abstract
The synthesis and reactivity of dialkynyldiboranes(4), a little-studied family of diboranes, are presented herein. Three dialkynyldiboranes(4) were prepared via two different salt metathesis pathways. The three reactive sites of these dialkynyldiboranes(4) are then selectively addressed by judicious application of reagents: addition of an amine N-oxide leads to oxygen insertion into the B–B bond, dicobaltoctacarbonyl binds to the alkynyl CC bonds, while Sonogashira–Hagihara cross-coupling conditions lead to double C–C bond formation at the alkynyl C–H groups.Keywords
Funding Information
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Deutsche Forschungsgemeinschaft
- Alexander von Humboldt-Stiftung
- Studienstiftung des Deutschen Volkes
This publication has 32 references indexed in Scilit:
- Diboron(4) Compounds: From Structural Curiosity to Synthetic WorkhorseChemical Reviews, 2016
- Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic EstersThe Journal of Organic Chemistry, 1995
- Diallenylborane als Edukte für BorheterocyclenEuropean Journal of Inorganic Chemistry, 1992
- Neuartige Allylboran- und Allyldiboran(4)-Derivate / Novel Allylboran- and Allyldiboran(4) DerivativesZeitschrift für Naturforschung B, 1990
- Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalystJournal of the Chemical Society, Chemical Communications, 1979
- Beiträge zur Chemie des bors XXVIII. Über die Einwirkung von Borhalogeniden auf Dibortetrakis(dimethylamid)Journal of Organometallic Chemistry, 1964
- Beiträge zur Chemie des Bors. XXI. Zur Kenntnis der Symmetrischen Dialkyl‐dibor‐bis‐dimethylamideZeitschrift für anorganische und allgemeine Chemie, 1963
- The Preparation and Properties of 1,2-Diethyl-1,2-bis-(dimethylamino)- and 1,2-Bis-(dimethylamino)-1,2-diphenyldiboronsInorganic Chemistry, 1962
- Tetra-(amino)-diborons1,2Journal of the American Chemical Society, 1960
- Der Zink‐Lichtbogen als ReduktionsmittelBerichte der deutschen chemischen Gesellschaft (A and B Series), 1925