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Photocatalytic reduction of aromatic azides to amines using CdS and CdSe nanoparticles

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Abstract

We have shown that CdS and CdSe nanoparticles can act as very efficient and highly chemoselective photocatalysts for the reduction of aromatic azides to aromatic amines. In several cases, the reaction proceeds with quantum yields near 0.5, which approaches the theoretical maximum for a two-electron process. The wide scope of the reaction was confirmed with compounds containing electron withdrawing (–NO2, CO2R, COR) and electron donating groups (–OMe,–R,–Cl) at the para-, meta-, and ortho-positions. Remarkably, the reaction is relatively insensitive to the electron demands of the substituent. However, azides with meta-substituents give slightly lower yields than those with the same substituent at the ortho- or para-position.

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Authors and Affiliations

  1. Departments of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095-1569, USA

    Manoj Warrier & Miguel A. Garcia-Garibay

  2. Chemical Engineering Department, University of California, Los Angeles, Los Angeles, CA, 90095-1592, USA

    Michael K. F. Lo & Harold Monbouquette

Authors
  1. Manoj Warrier
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  2. Michael K. F. Lo
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  3. Harold Monbouquette
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  4. Miguel A. Garcia-Garibay
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Corresponding author

Correspondence to Harold Monbouquette.

Additional information

Electronic supplementary information (ESI) available: The preparation of CdS and CdSe nanoparticles, the synthesis of aromatic azides, procedures for the photocatalyzed reduction of aromatic azides, and procedures for the quantum yield measurements. See http://www.rsc.org/suppdata/pp/b4/b404268a/

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Warrier, M., Lo, M.K.F., Monbouquette, H. et al. Photocatalytic reduction of aromatic azides to amines using CdS and CdSe nanoparticles. Photochem Photobiol Sci 3, 859–863 (2004). https://doi.org/10.1039/b404268a

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