Nickel-Catalyzed Electrophilic Amination of the Biphenylene C-C σ-Bond

Takeru Inoue; Soshi Nishino; Kosuke Yasui; Koji Hirano

doi:10.1021/acs.orglett.4c01226

Nickel-Catalyzed Electrophilic Amination of the Biphenylene C-C σ-Bond

Org Lett. 2024 May 24;26(20):4268-4273. doi: 10.1021/acs.orglett.4c01226. Epub 2024 May 14.

Authors

Takeru Inoue¹, Soshi Nishino¹, Kosuke Yasui^{1

2}, Koji Hirano^{1

2}

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
² Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan.

PMID: 38742804
DOI: 10.1021/acs.orglett.4c01226

Abstract

A nickel-catalyzed three-component carboamination of the biphenylene C-C σ-bond has been developed. Arylboronates and hydroxylamine derivatives work as carbon nucleophiles and nitrogen electrophiles, respectively, and the corresponding difunctionalized ring-opening products are obtained in good yields. The arylboronate nucleophile can be replaced with B₂pin₂ (boron nucleophile) and H-Si(OMe)₃ (hydride nucleophile), thus allowing for the aminoboration and hydroamination of the biphenylene C-C σ-bond under similar nickel catalysis.