1.
Org Lett
; 18(21): 5520-5523, 2016 11 04.
Article
in English
| MEDLINE
| ID: mdl-27768316
ABSTRACT
Lithiation reactions of tertiary benzylic esters and carbamates have been studied. Kinetic methodology revealed that a two-step reaction pathway should be considered for these reactions, where either the lithium precomplexation and/or the proton transfer steps can be rate determining. Kinetic isotopic effects were evaluated by comparison of the lithiations of the corresponding protio/deutero substrates, and the results obtained support the notion that lithium precomplexation is taking place on the reaction pathway and that it is the rate-determining step in this transformation.