Non-C₂-Symmetric <i>Bis</i>-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls

Abstract

A novel non-C2-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy in the C(sp2)–C(sp2) formation. Its catalytic activity in Suzuki–Miyaura cross-coupling reaction of unactivated aryl chlorides has been found to have high efficacy in 1 mol% Pd loading. This protocol demonstrated the potential on the synthesis of sterically hindered biaryls.

Keywords

• <i>bis</i>-benzimidazolium salt
• sterically hindered biaryls
• non-C₂-symmetric