Fluoride-Assisted Activation of Calcium Carbide: A Simple Method for the Ethynylation of Aldehydes and Ketones | Zendy

Abolfazl Hosseini | Zendy; Daniel Seidel | Zendy; Andreas Miska | Zendy; Peter R. Schreiner | Zendy

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Fluoride-Assisted Activation of Calcium Carbide: A Simple Method for the Ethynylation of Aldehydes and Ketones

Author(s) -

Abolfazl Hosseini,

Daniel Seidel,

Andreas Miska,

Peter R. Schreiner

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b01219

Subject(s) - chemistry , acetylide , calcium carbide , fluoride , calcium , organic chemistry , catalysis , combinatorial chemistry , inorganic chemistry , medicinal chemistry

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.

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