Journal article

Publication year: 2015

Pages: 2808-2811

Journal: Organic Letters

Volume number: 17

Issue number: 11

Open access status: Bronze

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

Publisher: 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 Citation style: 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 Citation style: 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