Hypervalent Iodine-Mediated Oxidative Rearrangement of N–H Ketimines: An Umpolung Approach to Amides

Hypervalent Iodine-Mediated Oxidative Rearrangement of N–H Ketimines: An Umpolung Approach to Amides

An umpolung approach to amides via hypervalent iodine-mediated oxidative rearrangement of N–H ketimines under mild reaction conditions is described. This strategy provides target amides with excellent selectivity in good yields. In addition, preliminary mechanistic studies demonstrated that the migr...

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Veröffentlicht in:Journal of organic chemistry 2017-11, Vol.82 (22), p.11848-11853
Hauptverfasser: Zhao, Zhenguang, Peng, Zhiyuan, Zhao, Yongli, Liu, Hao, Li, Chongnan, Zhao, Junfeng
Format: Artikel
Sprache:eng
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Zusammenfassung:An umpolung approach to amides via hypervalent iodine-mediated oxidative rearrangement of N–H ketimines under mild reaction conditions is described. This strategy provides target amides with excellent selectivity in good yields. In addition, preliminary mechanistic studies demonstrated that the migration preference depends on both steric and electronic effects of the migrating groups.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01468