General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids
Lauren R. Cafiero and Timothy S. Snowden*
*Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 35487-0336, Email: snowdenbama.ua.edu
L. R. Cafiero, T. S. Snowden, Org. Lett., 2008, 10, 3853-3856.
DOI: 10.1021/ol8016484 (free Supporting Information)
The reaction of aldehydes with trichloromethide followed by reductive ring opening under basic conditions affords homologated carboxylic acids in high yields. This operationally simple procedure provides a practical, efficient alternative to other homologation protocols and is compatible with sensitive aldehydes including enals and enolizable substrates.
see article for more examples
proposed reaction pathway
M. K. Gupta, Z. Li, T. S. Snowden, Org. Lett., 2014, 16, 1602-1605.
J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.