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. 2016 Jun 8;55(31):8928–8932. doi: 10.1002/anie.201603175

Table 1.

Counterion effect under optimized reaction conditions.[a] Inline graphic

NaOTf Yield [%][b]
(equiv) X=OTf X=PF6 X=BF4 X=OTs
0 94 91 18 18
0.5 68
1.0 86 94 87

[a] Reaction conditions: NaNO2 (0.16 mmol) was added to 1 (0.14 mmol) and NaOTf (0–1 equiv) in EtOAc (1 mL). The suspension was stirred at 70 °C for 16 hours. [b] Yield determined by 1H NMR analysis using 1,3,5‐trimethoxybenzene as internal standard. Tf=trifluoromethanesulfonyl.