20498-65-1Relevant academic research and scientific papers
Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles
Hollerbach, Michael R.,Barker, Timothy J.
, p. 1425 - 1427 (2018/05/24)
A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with s-butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the sec-butyl group, providing excellent yields of the benzylated products. 11B NMR experiments were performed to study the mechanism of this transformation.
Mechanistic criteria for cation radical reactions: Aminium salt-catalyzed cyclopropanation
Yueh, Wang,Bauld, Nathan L.
, p. 5671 - 5676 (2007/10/02)
Mechanistic studies of the cyclopropanation of a series of trans-stilbenes by ethyl diazoacetate catalyzed by two different triarylaminium salts decisively confirm a cation radical mechanism and rule out a hypothetical electrophilic mechanism. The elucidation of key aspects of these cation radical mechanisms, including kinetic vs equilibrium control of ionization and chain vs catalytic mechanisms, has also been achieved for these systems. New mechanistic criteria for the positive identification of cation radical mechanisms are proposed.
