A practical palladium catalyzed dehalogenation of aryl halides and α-haloketones

Fluorogenic Diversification of Unprotected Bromotryptophan by Aqueous Mizoroki–Heck Cross‐Coupling

“…Once the enzymatic halogenation taking place in phosphate puffer at pH 7.4 had gone to completion, the pH was increased by adding up to 5 equivalents of solid K 2 CO 3 to ensure sufficiently basic conditions for the cross‐coupling. However, under these conditions Pd‐catalyzed dehalogenation was observed as a side reaction . Consequently, the filtrate resulting from the enzymatic halogenation was concentrated from 1 to 5 m m in order to favor Mizoroki–Heck coupling over dehalogenation.…”

Highly Efficient and Monodisperse Graphene Oxide Furnished Ru/Pd Nanoparticles for the Dehalogenation of Aryl Halides via Ammonia Borane

“…[9, 10] Nowadays, heterogeneous catalysts have been upgraded for dehalogenation reactions, because the heterogeneous catalysts have several advantages; (i) the use of catalytic amount, (ii) recoverability, (iii) reusability, (iv) not to undergo the structural degradation, (v) value of the metal leaching into the reaction solution after reuse can be tolerated . For example, the heterogeneous/homogenous catalyst systems such as Pd/C, Pd(OAc) 2 /PPh 3 , palladium/imidazolium salt, indium(0) in ionic liquid (IL), indium(III)chloride, nickel complexes, nickel(0)/imidazolium chloride, Fe(acac) 3 were performed for the dehalogenation of various arylhalides in literature. However, the use of heterogenous catalyst is rare and those kind of promising works have led to the design of novel heterogeneous nanocatalytic systems for dehalogenation reactions.…”

Reductions of aryl bromides in water at room temperature

“…18 Previously, brominated piperonal 7 was dehalogentated by Chen and co-workers using Pd(OAc) 2 with triphenylphosphine in n -butanol at 100 °C. 19 By contrast, reactions utilizing this nanomicellar technology take place at ambient temperatures and afford high yields of products. It should be noted that while NaBH 4 is the inexpensive source of hydride, reagent formation takes place in situ and therefore, functional group compatibility, such as in the case of ketone 5 , is not a concern (and as shown for several other examples in Table 8; vide infra).…”