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. Author manuscript; available in PMC: 2022 Dec 15.
Published in final edited form as: J Am Chem Soc. 2021 Nov 30;143(49):21024–21036. doi: 10.1021/jacs.1c10932

Table 3:

Yields of XEC reactions between 1°, 2°, and benzylic Katritzky salts and alkyl iodides with different homogeneous reductants. Reaction conditions: 2-iodoanisole (0.03125 mmol), Katritzky salt (0.0375 mmol), reductant (0.0375 mmol), (dtbbpy)NiIIBr2 (10 mol%), in DMAc (0.25 mL) at 80 °C for 24 h. The yields were determined by integration of 1H NMR spectra against a hexamethylbenzene external standard.

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Reductant E° (V vs Fc) Yield (%) with
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Yield (%) with
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Yield (%) with
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Yield (%) with
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1 2 3 4
TPyE −1.32 77 34 57 25
TDAE −1.11 10 77 99 29
TAzE −1.09 <1 66 93 29
TPiE −1.06 <1 83 99 30
TME −0.85 <1 43 75 (93a) 90
a

5 mol% (dtbbpy)NiIIBr2 used.