Premium
Solvent‐Promoted Catalyst‐Free Nucleophilic Fluoroalkylation of Aldehydes
Author(s) -
Komoda Kazuki,
Shimokawa Ai,
Amii Hideki
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900456
Subject(s) - silanes , nucleophile , chemistry , catalysis , nucleophilic addition , fluoride , silane , trifluoromethyl , organic chemistry , solvent , polymer chemistry , inorganic chemistry , alkyl
Fluoroalkyl silanes are useful building blocks for nucleophilic introduction of fluoroalkyl groups into organic molecules. In general, fluoroalkyl silanes per se are stable compounds, but they are amenable to reactions as fluoroalkyl anion equivalents in the presence of base such as fluoride ion. Usually, KF acts as a good catalyst for nucleophilic fluoroalkylation of carbonyl compounds. To avoid the use of hygroscopic fluoride salts, we have developed a convenient catalyst‐free method for nucleophilic fluoroalkylation of aldehydes and ketones by the use of fluoroalkyl silanes. Trifluoromethyl(trimethyl)silane (Me 3 Si‐CF 3 ), and other fluoroalkyl silanes (Me 3 Si‐R f ) underwent solvent‐promoted nucleophilic addition to aldehydes smoothly to give fluoroalkylated alcohols in good yields. In the present reactions, the use of polar solvents such as DMSO, DMF or NMP is essential to the formation of 1,2‐adducts.