Journal article

Publication year: 2020

Pages: 4339-4346

Journal: European Journal of Organic Chemistry

Volume number: 2020

Issue number: 28

ISSN: 1434-193X

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/ejoc.202000612

Publisher: Wiley

Abstract: 
Ball milling of calcium carbide (CaC2) enables the reaction of its ethynyl moiety with organic electrophiles. This was realized simply by co-milling CaC(2)with organic substrates in a sealed jar without the need for an additive or a catalyst. Various ketones including those bearing alpha-hydrogens were ethynylated in good yields at short reaction times. Aryl halides are also amenable substrates for this protocol as they furnish aryl ethynes through a benzyne intermediate. This method offers a practical and cheap alternative to the established procedures for introducing ethynyl functionalities.

Harvard Citation style: Hosseini, A. and Schreiner, P. (2020) Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling, European Journal of Organic Chemistry, 2020(28), pp. 4339-4346. https://doi.org/10.1002/ejoc.202000612

APA Citation style: Hosseini, A., & Schreiner, P. (2020). Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling. European Journal of Organic Chemistry. 2020(28), 4339-4346. https://doi.org/10.1002/ejoc.202000612