Selective Hydrogenation by Carbocatalyst: The Role of Radicals Muhammad Sohail Ahmad, † Huixin He, § Yuta Nishina* †‡ †Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan §Department of Chemistry, Rutgers, the State University of New Jersey, Newark, NJ, 07102, USA ‡Research Core for Interdisciplinary Sciences, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700- 8530, Japan Table of Contents 1. General information------------------------------------------------------------------------------------------------------------------------- 1 2. Synthesis of NrGO --------------------------------------------------------------------------------------------------------------------------- 2 3. Structural analysis of NrGO--------------------------------------------------------------------------------------------------------------- 3 4. Elemental of the catalysts------------------------------------------------------------------------------------------------------------------- 3 5. General procedure for the hydrogenation of nitroarenes -------------------------------------------------------------------------- 4 6. General procedure for the hydrogenation of ketones -------------------------------------------------------------------------------- 4 7. Selective competitive experiment --------------------------------------------------------------------------------------------------------- 5 8. Representive procedure for the hydrogenation of nitroarenes -------------------------------------------------------------------- 5 9. Product identification ----------------------------------------------------------------------------------------------------------------------- 5 10. ESR study -------------------------------------------------------------------------------------------------------------------------------------- 7 11. Spin trap experiment ------------------------------------------------------------------------------------------------------------------------ 7 12. Method for the recyclability test ---------------------------------------------------------------------------------------------------------- 8 13. Screening test---------------------------------------------------------------------------------------------------------------------------------- 9 14. Proposed reaction pathway ---------------------------------------------------------------------------------------------------------------10 15. Recyclability of the catalyst ---------------------------------------------------------------------------------------------------------------10 16. 1 H nmr spectral charts of the aniline derivatives-------------------------------------------------------------------------------------12 17. GC-MS data for prodcuts measured by GC-FID -----------------------------------------------------------------------------------17 18. References -------------------------------------------------------------------------------------------------------------------------------------20 1. General Information All the chemicals used in this study were purchased from commercial sources and used as received unless otherwise mentioned. The surface chemistry and elemental analyses of the catalysts were performed using an X-ray photoelectron spectroscopy (XPS; JPS-9030) with a pass energy of 20 eV. The morphology of NrGO was measured using transmission electron microscopy (TEM; JEOL JEM-2100F), and the functional groups on the surface of the catalysts were recorded by Fourier-transform infrared spectrometry (FT-IR; Shimadzu IR Tracer 100). The samples for the FT-IR were dried and mixed with KBr, and then pressed into 1.3 cm-diameter pellets. Freeze-drying of the