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Metal-free Transformations of Nitrogen-oxyanions to Ammonia via Oxoammonium Salt.

Transformations of nitrogen-oxyanions  (NO x - ) to ammonia impart pivotal roles in sustainable biogeochemical processes . While metal mediated reductions of  NO x -  are relatively well known,  this report herein illustrates proton-assisted activations of  NO x -  anions in the presence of electron rich aromatics such as 1,3,5-trimethoxybenzene (TMB - H,  1a ) leading to the formation of oxoammonium salt [(TMB) 2 N + =O][NO 3 - ] ( 2a )  via  the intermediacy of NO + . Detailed characterizations including X-ray diffraction, multinuclear ( 1 H,  13 C,  15 N) NMR, and HRMS analyses on the metastable species  2a  disclose unambiguous structural and spectroscopic signatures. Oxoammonium salt  2a  exhibits 2e -  oxidative reactivity in the presence of oxidizable substrates such as benzyl amine, thiols, and ferrocene. Intriguingly, reaction of  2a with water affords ammonia.  Perhaps of the broader significance, this work reveals a new metal-free route germane to the conversion of NO x  to NH 3 .