Premium
Grignard Reactions in Pyridinium and Phosphonium Ionic Liquids
Author(s) -
Ford Leigh,
Atefi Farzad,
Singer Robert D.,
Scammells Peter J.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001468
Subject(s) - chemistry , pyridinium , phosphonium , ionic liquid , grignard reaction , solvent , diethyl ether , organic chemistry , yield (engineering) , alcohol , ether , ionic bonding , medicinal chemistry , catalysis , ion , materials science , reagent , metallurgy
Alkylpyridinium ( 10a , R = Me and 10b , R = Et) and tetraalkylphosphonium ( 19 ) ionic liquids which possess ether functionality were prepared and evaluated as solvents and co‐solvents for Grignard reactions. Interestingly, reduction of the starting aldehydes to the corresponding primary alcohol was the favored pathway when reactions were conducted in pyridinium ILs 10a , b in the absence an ethereal co‐solvent. However, the same reactions in the phosphonium IL 19 afforded the expected Grignard products in good yield in cases where diethyl ether was present as a co‐solvent.