Journal
NATURE COMMUNICATIONS
Volume 13, Issue 1, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/s41467-022-35394-z
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Funding
- National Natural Science Foundation of China [21871043, 1961130376]
- Department of Science and Technology of Jilin Province [20200801065GH, 20190701012GH, 20180101185JC]
- Fundamental Research Funds for the Central Universities [2412022XK003, 2412019ZD001, 2412020ZD003]
- Newton Trust [NAF\R1\191210]
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This study reports a chemoselective N-H insertion reaction of inexpensive aqueous ammonia using a TpBr3Ag-catalyzed two-phase system, leading to the conversion into value-added primary amines. The reaction exhibits high chemoselectivity and allows the coupling of inorganic nitrogen sources with diazo compounds or N-triftosylhydrazones to produce useful primary amines.
The conversion of inexpensive aqueous ammonia (NH3 center dot 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 center dot H2O using a TpBr3Ag-catalyzed two-phase system. Coordination by a homoscorpionate TpBr(3) ligand renders silver compatiblewithNH(3) 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.
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