General and practical conversion of aldehydes to homologated carboxylic acids.
The reaction of aldehydes with trichloromethide followed by sodium borohydride or sodium phenylseleno(triethyl)borate under basic conditions affords homologated carboxylic acids in high yields. This operationally simple procedure provides a practical, efficient alternative to other homologation protocols. The approach is compatible with sensitive aldehydes including enals and enolizable aldehydes. It also offers convenient access to alpha-monodeuterated carboxylic acids.
Cafiero
Lauren R
LR
Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 35487-0336, USA.
Snowden
Timothy S
TS