Alkyl Radical Coupling with Phenoxy(imine)–Nickel(II)–Aryl Complexes: Evidence for a Multistep Process in C–C Bond Formation

Hao Liang; L. Reginald Mills; Marina Pérez‐Jiménez; Matthew V. Joannou; Heejun Lee; Steven R. Wisniewski; Eric M. Simmons; Karla Ravin; Paul J. Chirik

doi:10.1021/jacs.6c02912

April 27, 2026Journal of the American Chemical SocietyOpen Access

Alkyl Radical Coupling with Phenoxy(imine)–Nickel(II)–Aryl Complexes: Evidence for a Multistep Process in C–C Bond Formation

View Full Paper

Ask AI

Bookmark

Share

Key Points

The study aims to investigate the mechanism of C-C bond formation using phenoxy(imine)-nickel(II)-aryl complexes.
Measured C kinetic isotope effects and conducted computational studies to assess the reaction pathway.
Treated nickel(II)-aryl complexes with oxidants to generate and detect transient nickel(III) complexes using EPR spectroscopy.
Utilized organozinc reagents to intercept the nickel(III) complexes for product formation.
Transient nickel(III) complexes were successfully detected by EPR spectroscopy.
C-C bond formation products were generated when organozinc reagents intercepted the nickel(III) complexes.
The findings support a multistep process involving different oxidation states.

Implication

Examines C-C bond formation in alkyl radical coupling, suggesting a multistep process.

Abstract

C kinetic isotope effect measurements and computational studies are also consistent with this pathway. Treatment of phenoxy(imine)-nickel(II)-aryl complexes with various oxidants generated transient nickel(III) complexes that were detected by electron paramagnetic resonance (EPR) spectroscopy and intercepted by organozinc reagents to generate C-C bond formation products, supporting the intermediacy of this oxidation state in the overall process.

Discussion

No takes yet. Share an insight, caveat, or question.

Cite This Study

Liang et al. (2026) studied this question.

synapsesocial.com/papers/69f2f0991e5f7920c6386bcc https://doi.org/10.1021/jacs.6c02912

View Full Paper

Ask AI

Bookmark

Share

Alkyl Radical Coupling with Phenoxy(imine)–Nickel(II)–Aryl Complexes: Evidence for a Multistep Process in C–C Bond Formation

Key Points

Implication

Abstract

Discussion

Cite This Study

Alkyl Radical Coupling with Phenoxy(imine)–Nickel(II)–Aryl Complexes: Evidence for a Multistep Process in C–C Bond Formation

Key Points

Implication

Abstract

Discussion

Cite This Study

Keep reading

Keep reading