Diethyl boronobenzylphosphonates as substrates in Petasis reaction

Abstract

The Petasis reaction of α-(N-benzylamino)boronobenzylphosphonates with amines and salicylaldehyde or glyoxalic acid gives the desired products in moderate to good yields. The efficiency of the reaction is strongly dependent on the structure of the amine.

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

“…86 In addition to the arylboronic acids used in this study, a wide range of boronic acid components have also been employed in PRs with salicylaldehydes and secondary amines, such as boronobenzylphosphonates. 87…”

“… The developed method was applied for the synthesis of the core scaffold of BIIB042, a γ-secretase modulator with potential applications in the treatment of Alzheimer’s disease . In addition to the arylboronic acids used in this study, a wide range of boronic acid components have also been employed in PRs with salicylaldehydes and secondary amines, such as boronobenzylphosphonates …”

“…86 In addition to the arylboronic acids used in this study, a wide range of boronic acid components have also been employed in PRs with salicylaldehydes and secondary amines, such as boronobenzylphosphonates. 87 Alkylaminophenols with core scaffold 28 could also be generated through cobalt ferrite nanoparticle-catalyzed PRs. 76 Another series of similar diphenylmethanamines, generally containing a morpholino instead of a pyrrolidino alkyl moiety, was synthesized using a catalysis based on chitosan or trititanate nanotubes in high yield.…”