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Silver-Catalyzed ortho-Selective C-H Selenylation of N-Alkylanilines
Xiaochun Cao1, Ran He1, Junlong Li1
1Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics School of pharmacy, Chengdu University, Chengdu 610106, People's Republic of China.
Abstract:
A silver-catalyzed C(sp2)-H selenylation of readily available N-alkylanilines with diaryl diselenides in a one-pot process has been developed. This protocol relies on the use of a removable N-nitroso directing group and demonstrates excellent regio-selectivity and broad functional group tolerance, affording the valuable ortho-selenylated N-nitroso anilines up to 96% yields. Notably, the selenylation products can be further transformed into bioactive selenazepinone scaffold. A plausible radical pathway is proposed based on the preliminary mechanistic studies for understanding this novel selenylation.
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