Chemoselective carbene insertion into the N−H bonds of NH3·H2O

Zhaohong Liu, Yong Yang, Qingmin Song, Linxuan Li, Giuseppe Zanoni, Shaopeng Liu, Meng Xiang, Edward A. Anderson and Xihe Bi ()
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Zhaohong Liu: Northeast Normal University
Yong Yang: Northeast Normal University
Qingmin Song: Northeast Normal University
Linxuan Li: Northeast Normal University
Giuseppe Zanoni: University of Pavia
Shaopeng Liu: Northeast Normal University
Meng Xiang: Northeast Normal University
Edward A. Anderson: University of Oxford
Xihe Bi: Northeast Normal University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract The conversion of inexpensive aqueous ammonia (NH3·H2O) into value-added primary amines by N−H insertion persists as a longstanding challenge in chemistry because of the tendency of Lewis basic ammonia (NH3) to bind and inhibit metal catalysts. Herein, we report a chemoselective carbene N−H insertion of NH3·H2O using a TpBr3Ag-catalyzed two-phase system. Coordination by a homoscorpionate TpBr3 ligand renders silver compatible with NH3 and H2O and enables the generation of electrophilic silver carbene. Water promotes subsequent [1,2]-proton shift to generate N−H insertion products with high chemoselectivity. The result of the reaction is the coupling of an inorganic nitrogen source with either diazo compounds or N-triftosylhydrazones to produce useful primary amines. Further investigations elucidate the reaction mechanism and the origin of chemoselectivity.

Date: 2022
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DOI: 10.1038/s41467-022-35394-z

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