Pure Appl. Chem., 2013, Vol. 85, No. 6, pp. 1089-1101
http://dx.doi.org/10.1351/PAC-CON-12-10-11
Published online 2013-04-10
The new world of organic reactions in water
Abstract:
Different reactivities and selectivities are observed in water compared with those in organic solvents. In this article, such three examples are described. While ammonia was known not to react in metal-catalyzed allylic amination, palladium-catalyzed allylic amination using aqueous ammonia proceeded to afford primary amines in high yields. Second, allylboronates reacted with aldehydes in aqueous media to afford α-addition adducts exclusively in high yields with high diastereo- and enantioselectivities using Zn(OH)2 with ligands as catalysts. Finally, it was found that catalytic use of In(0) was effective for the reactions of allylboronates with ketones in water.
Keywords
allylation; allylic amination; asymmetric catalysis; C–C bond formation; green sustainable chemistry; water.