Journalartikel

Jahr der Veröffentlichung: 2015

Seiten: 2808-2811

Zeitschrift: Organic Letters

Bandnummer: 17

Heftnummer: 11

Open Access Status: Bronze

DOI Link: https://doi.org/10.1021/acs.orglett.5b01219

Verlag: American Chemical Society

Abstract: 

The fluoride-assisted ethynylation of ketones and aldehydes is described
using commercially available calcium carbide with typically 5 mol % of
TBAF·3H₂O as the catalyst in DMSO. Activation of calcium
carbide by fluoride is thought to generate an acetylide “ate”-complex
that readily adds to carbonyl groups. Aliphatic aldehydes and ketones
generally provide high yields, whereas aromatic carbonyls afford
propargylic alcohols with moderate to good yields. The use of calcium
carbide as a safe acetylide ion source along with economic amounts of
TBAF·3H₂O make this procedure a cheap and operationally simple method for the preparation of propargylic alcohols.

Harvard-Zitierstil: Hosseini, A., Seidel, D., Miska, A. and Schreiner, P. (2015) Fluoride-Assisted Activation of Calcium Carbide: A Simple Method for the Ethynylation of Aldehydes and Ketones, Organic Letters, 17(11), pp. 2808-2811. https://doi.org/10.1021/acs.orglett.5b01219

APA-Zitierstil: Hosseini, A., Seidel, D., Miska, A., & Schreiner, P. (2015). Fluoride-Assisted Activation of Calcium Carbide: A Simple Method for the Ethynylation of Aldehydes and Ketones. Organic Letters. 17(11), 2808-2811. https://doi.org/10.1021/acs.orglett.5b01219