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. Author manuscript; available in PMC: 2019 Jun 20.
Published in final edited form as: J Am Chem Soc. 2018 Jun 11;140(24):7667–7673. doi: 10.1021/jacs.8b03744

Figure 2.

Figure 2

Kinetic Isotopic Effect (KIE) Experiment. The rate of C–N cross-coupling was compared between piperidine and piperidine-d11 using 4-bromobenzotrifluoride as the coupling partner. Reactions conditions: 1.0 equiv of 4-bromobenzotrifluoride (0.4 mmol), 3.5 equiv of piperidine (H or D), 5 mol% NiBr2·3H2O, and irradiation at 365 nm. The observed rate constant (kobs) was determined by solving a second-order rate equation model via numerical integration (RK4 method, Figures S23 and S24); inhibition periods of 6 and 52 min were included in the model fitting of piperidine and piperidine-d11, respectively.