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Solid Supported Palladium(0) Nanoparticles: An Efficient Heterogeneous Catalyst for Regioselective Hydrosilylation of Alkynes and Suzuki Coupling of β-Arylvinyl Iodides

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Abstract

The solid supported palladium(0) nanoparticles (NPs) were found as an active heterogeneous catalyst for regioselective hydrosilylation of alkynes with organosilanes in the presence of NaI as additive. Aliphatic as well as aromatic terminal/substituted alkynes with both electron releasing and withdrawing functionalities similarly participated in the hydrosilylation to produce regioselective β-isomers of vinylsilanes under mild reaction conditions. Reducible functional groups such as nitrile, ester, halide, alkene and alkyne were also found to be tolerated under this condition. Furthermore, the triethylsilylstyrene was applied for consecutive iododesilylation followed by Suzuki coupling reaction to produce stilbenes. The air/moisture stable SS–Pd catalyst was recycled for hydrosilylation reaction up to ten runs without significant loss of its catalytic activity.

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Solid Supported Palladium(0) Nanoparticles: An Efficient Heterogeneous Catalyst for Regioselective Hydrosilylation of Alkynes and Suzuki Coupling of β-Arylvinyl Iodides

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Acknowledgments

Authors are grateful to Director CSIR-IHBT for providing necessary facilities during the course of the work. We gratefully acknowledge AIRF-JNU for HRTEM analysis. The authors thank CSIR, New Delhi for financial support as part of XII Five Year Plan programme under title ORIGIN (CSC-0108). CBR (UGC-JRF), AKS (CSIR-SRF), NRG (UGC-SRF) and DS (CSIR-SRF) thanks CSIR and UGC New Delhi for awarding fellowships.

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Authors and Affiliations

  1. Natural Plant Products Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, 176061, Himachal Pradesh, India

    C. Bal Reddy, Arun K. Shil, Nitul Ranjan Guha, Dharminder Sharma & Pralay Das

  2. Academy of Scientific & Innovative Research, New Delhi, India

    C. Bal Reddy, Arun K. Shil, Nitul Ranjan Guha & Pralay Das

Authors
  1. C. Bal Reddy
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  2. Arun K. Shil
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  3. Nitul Ranjan Guha
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  4. Dharminder Sharma
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  5. Pralay Das
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Corresponding author

Correspondence to Pralay Das.

Additional information

CSIR-IHBT communication no. 3546

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Bal Reddy, C., Shil, A.K., Guha, N.R. et al. Solid Supported Palladium(0) Nanoparticles: An Efficient Heterogeneous Catalyst for Regioselective Hydrosilylation of Alkynes and Suzuki Coupling of β-Arylvinyl Iodides. Catal Lett 144, 1530–1536 (2014). https://doi.org/10.1007/s10562-014-1311-8

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  • DOI: https://doi.org/10.1007/s10562-014-1311-8

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