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- Title
Chemoselective carbene insertion into the N−H bonds of NH<sub>3</sub>·H<sub>2</sub>O.
- Authors
Liu, Zhaohong; Yang, Yong; Song, Qingmin; Li, Linxuan; Zanoni, Giuseppe; Liu, Shaopeng; Xiang, Meng; Anderson, Edward A.; Bi, Xihe
- 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. Converting low-cost inorganic chemicals into value-added organic chemicals is a longstanding goal in chemistry. Here the authors describe a silver-catalysed chemoselective carbene N−H insertion reaction, providing access to primary amines from aqueous ammonia and diazo compounds.
- Subjects
INORGANIC compounds; CHEMOSELECTIVITY; ORGANIC compounds; AMMONIA compounds; DIAZO compounds; METAL catalysts; NITROGEN
- Publication
Nature Communications, 2022, Vol 13, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-022-35394-z