Affiliation:
1. Department of Chemistry, University of Rochester, Rochester, NY 14627, USA
Abstract
A single-step method for aniline formation was examined. Using a vanadate catalyst with an iron oxide co-catalyst and hydroxylamine hydrochloride as the amine source, an up to 90% yield of aniline was obtained with high selectivity. Further study showed that the overall reaction was pseudo-second order in terms of hydroxylamine concentration. Regioselective H-D exchange experiments suggest that the C-N bond formation step occurs via an irreversible electrophilic pathway. Based on all of the key observations, a mechanism is proposed.
Funder
National Science Foundation under the CCI Center for Enabling New Technologies through Catalysis
Subject
Organic Chemistry,Inorganic Chemistry,Electrochemistry,Chemistry (miscellaneous)
Reference25 articles.
1. (2015, May 21). Grand View Research Aniline Market Analysis. Grand View Research. Available online: http://www.grandviewresearch.com/industry-analysis/aniline-market.
2. Parshall, G.W., and Ittel, S.D. (1992). Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes, Wiley. [2nd ed.].
3. Photocatalytic Hydrogen-Evolution Cross-Couplings: Benzene C–H Amination and Hydroxylation;Zheng;J. Am. Chem. Soc.,2016
4. Application of combinatorial catalysis for the direct amination of benzene to aniline;Desrosiers;Catal. Today,2003
5. Nitric oxide is an obligate bacterial nitrification intermediate produced by hydroxylamine oxidoreductase;Caranto;Proc. Nat. Acad. Sci. USA,2017