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. Author manuscript; available in PMC: 2021 Sep 2.
Published in final edited form as: J Am Chem Soc. 2020 Aug 24;142(35):15027–15037. doi: 10.1021/jacs.0c06139

Figure 1.

Figure 1.

(A) Comparison of reaction time courses as measured by reaction calorimetry for the reaction shown with catalysts OA1–OA6 (Ar = 4-(2-(trimethylsilyl)ethyl benzoate)). (B) 31P NMR spectrum of the reaction employing OA1 as the precatalyst after 1 h. Reaction conditions: 1.0 mmol 2-bromo-1,4-dimethylbenzene, 1.4 mmol n-propylamine, 1.4 mmol NaOt-Bu, 0.1 mmol n-dodecane (internal standard), 2.5 or 5.0 μmol OAn in THF (1.0 M [2-bromo-1,4-dimethylbenzene]) maintained at 26.0 °C in OmniCal calorimeter. Note: OA1 refers to precatalyst with L1, OA2 to that with L2, etc. Reaction GC conversions for each catalyst: OA1 = 9%, OA2 = 9%, OA3 = 60%, OA4 = 65%, OA5 = 90%, OA6 = 96%.