Photoredox/Iron Dual-Catalyzed Insertion of Acyl Nitrenes into C–H Bonds

In this work, the use of N-acyloxybenzamides as efficient acyl nitrene precursors under photoredox/iron dual catalysis is reported. The resulting acyl nitrenes could be captured by various types of C–H bonds and S- or P-containing molecules. Mechanism investigations suggested that the formation of t...

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Veröffentlicht in:Organic letters 2022-06, Vol.24 (23), p.4114-4118
Hauptverfasser: Hou, Ming, Zhang, Zhide, Lai, Xiaojing, Zong, Qianshou, Jiang, Xinpeng, Guan, Meng, Qi, Rui, Qiu, Guanyinsheng
Format: Artikel
Sprache:eng
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Zusammenfassung:In this work, the use of N-acyloxybenzamides as efficient acyl nitrene precursors under photoredox/iron dual catalysis is reported. The resulting acyl nitrenes could be captured by various types of C–H bonds and S- or P-containing molecules. Mechanism investigations suggested that the formation of the acyl nitrene from the N-acyloxybenzamide occurs by a photoredox process, and it is believed that in this redox process oxidative N–H bond cleavage of the N-acyloxybenzamide occurs prior to reductive N–O bond cleavage of the N-acyloxybenzamide.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01176