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Iron and Palladium(II) Phthalocyanines as Recyclable Catalysts for Reduction of Nitroarenes

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Abstract

Iron(II) and palladium(II) phthalocyanines have been established as recyclable heterogeneous catalysts for the reduction of aromatic nitro compounds to corresponding amines using diphenylsilane/sodium borohydride as hydrogen sources in ethanol. Various reducible functional groups, such as acetyl, ester, cyano, amide, sulphonamide and carboxylic acid etc. were well tolerated, and the methods were applicable up to gram scale. Mechanistic studies showed that reduction of nitro group proceed through direct (nitroso) pathway and possibly iron or palladium phthalocyanines activates nitro group for reduction. FePc and PdPc also catalyzed the generation of hydrogen from the combination of diphenylsilane/sodium borohydride and ethanol.

Graphical Abstract

Iron and palladium (II) phthalocyanines has been established as an efficient recyclable catalytic systems for reduction of nitroarenes with green solvent system. Various nitro substituted aromatics and heteroaromatics has been successfully reduced to corresponding amines in good to excellent yields. The present methods have also been productively applicable for gram scale reactions.

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Acknowledgments

Authors are grateful to Director of the institute for providing necessary facilities. Financial support received from CSIR-India (fellowship to P. K. V) and DST under Fast Track Scheme (U. S.) is gratefully acknowledged.

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Authors and Affiliations

  1. Natural Plant Products Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, 176 061, Himachal Pradesh, India

    Praveen Kumar Verma, Manju Bala, Kavita Thakur, Upendra Sharma, Neeraj Kumar & Bikram Singh

  2. Academy of Scientific & Innovative Research, CSIR-Institute of Himalayan Bioresource Technology, Palampur, 176 061, Himachal Pradesh, India

    Praveen Kumar Verma, Manju Bala & Bikram Singh

  3. Department of Chemistry, Korea Advanced Institute of Science & Technology (KAIST), Daejeon, 305-701, South Korea

    Upendra Sharma

Authors
  1. Praveen Kumar Verma
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  2. Manju Bala
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  3. Kavita Thakur
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  4. Upendra Sharma
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  5. Neeraj Kumar
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Correspondence to Bikram Singh.

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CSIR-IHBT Communication No. 3564.

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Verma, P.K., Bala, M., Thakur, K. et al. Iron and Palladium(II) Phthalocyanines as Recyclable Catalysts for Reduction of Nitroarenes. Catal Lett 144, 1258–1267 (2014). https://doi.org/10.1007/s10562-014-1269-6

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  • DOI: https://doi.org/10.1007/s10562-014-1269-6

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