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20.5.1.7.6.5 Method 5: Hydrostannation

DOI: 10.1055/sos-SD-020-00774

Zhang, M.; Hanson, P. R.Science of Synthesis, (200720900.

Baba and co-workers[‌192‌] reported that bromomagnesium(1+) bromo(dibutyl)hydrido(iodo)stannate(1) (162), prepared by mixing of dibutyl(iodo)stannane and magnesium bromidediethyl ether complex in ethyl acetate, effectively reacts with α,β-unsaturated esters 161 and produces conjugate reduction products 163 in high chemoselectivity (Scheme 45). Terminally monosubstituted α,β-unsaturated esters 161 are reduced effectively to the corresponding saturated esters 163, and the reducible functionalities such as nitro and halogen groups remain unchanged (Scheme 45). The formation of the ate complex bromomagnesium(1+) bromo(dibutyl)hydrido(iodo)stannate(1) is essential for conjugate hydrostannation, since none of the systems tributylstannane, dibutyl(iodo)stannane, lithium (dibutyl)hydridodiiodostannate(1), or dibutyl(iodo)stannane/boron trifluoridediethyl ether complex works for this reaction.

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References


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