Journal of Organic Chemistry p. 3232 - 3238 (2017)
Update date:2022-09-26
Topics:
Wu, Si-Yi
Ma, Xiao-Pan
Liang, Cui
Mo, Dong-Liang
An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.
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