Synthesis of 3‐Aryl‐5‐t‐butylsalicylaldehydes and their Chiral Schiff Base Compounds

Abstract

Six meta‐substituted salicylaldehyde compounds have been prepared in 68–90% yields by the Suzuki–Miyaura coupling reaction using 3‐bromo‐5‐t‐butylsalicylaldehyde (1a) and arylboronic acids (2a–f) as reactants. Among the obtained products, 3‐(4‐fluorophenyl)‐5‐t‐butylsalicylaldehyde (3b), 3‐(4‐methylphenyl)‐5‐t‐butylsalicylaldehyde (3d), 3‐(1‐naphthyl)‐5‐t‐butylsalicylaldehyde (3e), and 3‐(2‐naphthyl)‐5‐t‐butylsalicylaldehyde (3f) have not been reported so far. A series of new Schiff base ligands (L1–L10) were obtained in 51–89% yields from these salicylaldehyde derivatives.

Keywords:

• 3‐bromo‐5‐t‐butylsalicylaldehyde
• chiral Schiff base ligands
• meta‐substituted salicylaldehyde
• Suzuki–Miyaura coupling reaction

Acknowledgments

We are grateful to the Chinese National Natural Science Foundation (Grant Nos. 20471013 and 20633020), the Swedish Energy Agency, the Swedish Research Council, and the K & A Wallenberg Foundation for financial support of this work.