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

Autor:	Abolfazl Hosseini, Daniel Seidel, Peter R. Schreiner, Andreas Miska
Rok vydání:	2015
Předmět:	chemistry.chemical_compound chemistry Calcium carbide Acetylide Organic Chemistry Organic chemistry Physical and Theoretical Chemistry Biochemistry Fluoride Catalysis
Zdroj:	Organic Letters. 17:2808-2811
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.5b01219
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6f9905596eaf81856a9494e394a74958 https://doi.org/10.1021/acs.orglett.5b01219 Zobrazit plný text záznamu