Development of highly active metal catalysts based on bicyclic NHC ligands

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K18832
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Kumamoto University
• Principal Investigator: Ando Shin 熊本大学, 大学院生命科学研究部(薬), 助教 (00622599)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 遷移金属触媒 / 含窒素複素環式カルベン / 銅 / ニッケル / カップリング反応

Outline of Final Research Achievements

NHC ligands are generally equipped with bulky N-substituents, while our bicyclic NHC possess a bulky phenyl ring on the non-carbenic carbons. In this study, we applied our novel NHC ligands to transitional metal catalysts and investigated the effects of the unique steric properties.
The copper complexes supported by our NHCs were stable on a bench and successfully catalyzed the borylation of arylbromide. In this catalysis, the bicyclic NHC ligand showed significantly higher reactivity toward hindered substrates than ubiquitous NHCs, which indicates that the bicyclic NHC is bulky but accessible. On the nickel catalysis, our ligand effectively worked for the Kumada-Tamao-Corriu coupling of arylboromides with tertiary alkyl Grignard reagents. We also developed the stable NHC-Ni precatalyst which finely worked for Suzuki-Miyaura cross-coupling.

Free Research Field

有機化学