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. Author manuscript; available in PMC: 2021 Mar 18.
Published in final edited form as: J Am Chem Soc. 2020 Mar 9;142(11):5117–5125. doi: 10.1021/jacs.9b12320

Table 4.

Directing Group Evaluation for α-C(sp3)‒H Alkylation of Piperidine.a,b

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a

Reaction conditions: 4a-1 to 4a-4 (0.1 mmol, 1.0 equiv), [Ir(cod)Cl]2 (0.005 mmol, 0.05 equiv), AgOTf (0.01 mmol, 0.1 equiv), ethyl acrylate (0.8 mmol, 8.0 equiv), HBF4.Et2O (0.01 mmol, 0.1 equiv), degassed PhCl (0.5 mL), 85 °C, under Ar, 24 h.

b

Yields were determined by 1H NMR analysis of the crude products using mesitylene as the internal standard.