T. Tsukinoki et al., Organic reaction in water. Part 4. New synthesis of vicinal diamines usingzinc powder-promoted carbon-carbon bond formation, GREEN CHEM, 2(3), 2000, pp. 117-119
Reductive coupling of aromatic imines is performed by the use of zinc powde
r and additives such as NH4Cl and L-tyrosine in water without any organic s
olvents under mild conditions to give the corresponding vicinal diamines in
good yields; cross-coupling of N-benzylideneaniline and benzaldehyde simil
arly proceeds in aqueous media to afford the corresponding 2-aminoalcohol.