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Ni(II)/Al(0) mediated benzylic \(\hbox {Csp}^{3}\)-\(\hbox {Csp}^{3}\) coupling in aqueous media

  • Mukesh Kumar Nayak
  • Priyabrata Mukhi
  • Anuradha Mohanty
  • Sohel Samim Rana
  • Rajat Arora
  • Himani Narjinari
  • Sujit RoyEmail author
Regular Article
  • 14 Downloads

Abstract

Abstract

The reaction of benzyl bromides and chlorides with aluminium metal powder or foil (1.2 eqv.) in the presence of catalytic nickel nitrate (10 mol%) in water at room temperature resulted in homocoupling to the corresponding bibenzyl products which were isolated in moderate to good yields. In sharp contrast, the same reaction in organic solvents like dichloromethane, dimethylformamide, acetonitrile, methanol and toluene yielded only a trace amount of the desired product. The scope of the reaction was tested with substituents on the aromatic ring such as Me-, Cl-, CN-, F-, \(\hbox {NO}_{2}\)-, Ph- as well as \(2{^{\circ }}\) benzyl halides.

Graphical abstract

The reagent combination of aluminium metal and catalytic \(\hbox {Ni}(\hbox {NO}_{3})_{2}\) promotes the homocoupling of benzyl bromides and chlorides giving rise to the corresponding bibenzyl products in good to excellent yields. The reaction is greatly facilitated in water and showed good functional group tolerance. Besides the mild reaction condition and bench-friendliness, the present reaction constitutes the first example of aluminium-mediated homocoupling of a halide in water.

Keywords

C-C bond formation reaction in water aluminium nickel benzyl halide 

Notes

Acknowledgements

The authors thank the Institute for support including fellowship.

Supplementary material

12039_2019_1638_MOESM1_ESM.pdf (733 kb)
Supplementary material 1 (pdf 733 KB)

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Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  1. 1.School of Basic SciencesIndian Institute of Technology BhubaneswarArgul, KhurdaIndia

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