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- Title
Ni(II)/Al(0) mediated benzylic Csp3-Csp3 coupling in aqueous media.
- Authors
Nayak, Mukesh Kumar; Mukhi, Priyabrata; Mohanty, Anuradha; Rana, Sohel Samim; Arora, Rajat; Narjinari, Himani; Roy, Sujit
- 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-, NO 2 -, Ph- as well as 2 ∘ benzyl halides. The reagent combination of aluminium metal and catalytic Ni (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.
- Subjects
METAL chlorides; BENZYL bromide; BENZYL halides; DICHLOROMETHANE; ORGANIC solvents
- Publication
Journal of Chemical Sciences, 2019, Vol 131, Issue 7, pN.PAG
- ISSN
0974-3626
- Publication type
Article
- DOI
10.1007/s12039-019-1638-1