Journal
DALTON TRANSACTIONS
Volume 51, Issue 4, Pages 1553-1560Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1dt03107d
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Funding
- National Natural Science Foundation of China [21905275, 22025206, 21802137]
- DICP [DICP I202009]
- Liaoning Revitalization Talents Prograrn [XLYC2002012]
- Dalian Innovation Support Plan for High Level Talents [2020RT10]
- Dalian Science and Technology Innovation Fund [2019J11CY009]
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An efficient approach for the synthesis of arylamines from nitroarenes and hydrazine using an iron-molybdenum sulfide catalyst has been presented. The study reveals that the reduction of the nitro group to the nitroso group is the rate-determining step, and it is confirmed that the active H* should be in polar states.
We herein present an efficient approach for the chemoselective synthesis of arylamines from nitroarenes and hydrazine over an iron-molybdenum sulfide catalyst ([FeMo]S-x). The heterogeneous hydrogen transfer reduction can be efficiently carried out at 30 degrees C and provides anilines with 95-99% selectivities. The in situ gas product analysis demonstrates that [FeMo]S-x can catalyze the decomposition of N2H4 to H* species, not H-2. Combining with the kinetic analysis of the aniline generation rates from nitrobenzene and intermediates, the nitro group reduction to the nitroso group is confirmed to be the rate-determining step. The positive slope of Hammett's equation suggests that the critical intermediate in the rate-determining step is in the negative state, which suggests that the active H* should be in polar states (H delta- and H delta+). These findings will provide a novel route for the synthesis of substituted anilines and broaden the application of MoSx catalysts under mild conditions.
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