Fig 1.
Identification of a byproduct from a palladium catalyzed aryl amination reaction.
Table 1.
Optimization of reaction temperature and time.*
Table 2.
Optimization of the amount of nucleophile and the effect of the counterion of t-butoxide.*
Table 3.
Optimization of the reaction concentration.*
Table 4.
Effect of the solvent.*
Fig 2.
SNAr reaction of 2,4-dimethoxynitrobenzene with tert-butoxide.
Fig 3.
X-ray crystal structure of 3.
Fig 4.
Transetherification of o-methoxynitrobenzenes with sodium tert-butoxide.
*Methods: A. nitrobenzene derivative (0.3 mmol) and NaOtBu (2.1 mmol) in 10% DME in toluene (1.5 mL) at 110°C for 20 min under microwave irradiation. B. nitrobenzene derivative (0.3 mmol) and NaOtBu (2.1 mmol) in toluene (1.5 mL) at 110°C for 20 min under microwave irradiation. C. nitrobenzene derivative (0.3 mmol) and NaOtBu (0.6 mmol) in toluene (1.5 mL) at room temperature for 5 d. ** Isolated yield after purification.
Fig 5.
Proposed mechanism for the formation of 2 and 3.
Fig 6.
SNAr reactions of sodium ethoxide and sodium cyclohexanolate.
Fig 7.
Summary of reaction conditions.