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.
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Nayak, M.K., Mukhi, P., Mohanty, A. et al. Ni(II)/Al(0) mediated benzylic \(\hbox {Csp}^{3}\)-\(\hbox {Csp}^{3}\) coupling in aqueous media. J Chem Sci 131, 59 (2019). https://doi.org/10.1007/s12039-019-1638-1
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DOI: https://doi.org/10.1007/s12039-019-1638-1