A New Method for the Cleavage of Nitrobenzyl Amides and Ethers.
A mild and efficiento- andp-nitrobenzyl cleavage protocol was developed.o- andp-Nitrobenzyl groups were easily removed from a variety of substrates using 20% aqueous NaOH in methanol at 75 °C, presumably via oxidation at the benzylic position by oxygen dissolved in the solution. These easily introducible and removable nitrobenzyl groups can serve as valuable protecting groups for the synthesis of multifunctional, complex molecules.
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Boulevard, MC 101-20, Pasadena, CA 91125, USA.
Seo-Jung
SJ
Han
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Boulevard, MC 101-20, Pasadena, CA 91125, USA.
Gabriel Fernando
GF
de Melo
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Boulevard, MC 101-20, Pasadena, CA 91125, USA.
Brian M
BM
Stoltz
Amide protection; Deprotection; Protecting group; o-Nitrobenzyl group; p-Nitrobenzyl group