The salt-free nickel-catalysed α-allylation reaction of ketones with allyl alcohol and diallylether

Abstract

The alpha-allylation of ketones will allyl alcohol was performed thanks to the use of nickel-based catalysts. No base nor additive needed!

Efficient and Clean Nickel Catalyzed α‐Allylation Reaction of Nitriles

“…As we previously reported for the allylation of ketones, [10] diallylether 9 a could also be involved in that reaction. As example with 2,2‐diphenylacetonitrile 5 a , a good isolated yield of 80% was then obtained by using 1 equivalent of diallylether 9 a (Scheme 3).…”

“…To activate allylic alcohols, catalytic amounts of transition metals are generally needed [5] . We reported very simple protocols of Ni‐catalyzed allylic alkylation with allylic alcohol for the transformation of nucleophiles such as amides, [6] ketoesters and diketones, [7] malonates, [8] aldehydes [9] and ketones [10] . Beyond the use of more precious metals such as palladium, [11] iridium, [12] ruthenium, [13] platinum [14] and rhodium, [15] the use of nickel has opened up interesting prospects.…”

“…[5] We reported very simple protocols of Ni-catalyzed allylic alkylation with allylic alcohol for the transformation of nucleophiles such as amides, [6] ketoesters and diketones, [7] malonates, [8] aldehydes [9] and ketones. [10] Beyond the use of more precious metals such as palladium, [11] iridium, [12] ruthenium, [13] platinum [14] and rhodium, [15] the use of nickel has opened up interesting prospects. This metal is abundant and inexpensive and it is noteworthy that nickel based catalysts prevent the addition of bases or other additives.…”

“…This metal is abundant and inexpensive and it is noteworthy that nickel based catalysts prevent the addition of bases or other additives. [16] The highly efficient α-allylation of carbonyl compounds obtained with nickel-based catalysts [7][8][9][10] opens the question of the reactivity of nitriles (Scheme 1).…”

Synergistic effect of GO/SrFe12O19 as magnetic hybrid nanocatalyst for regioselective ring-opening of epoxides with amines under eco-friendly conditions

“…Moreover, water as a solvent promotes hydrogen bonding with the oxygen of epoxides which enhances the electrophilicity of the carbon in the alpha position. 80 …”