A Recyclable Electrochemical Allylation in Water

Abstract

To develop environmentally benign processes for C-C bond formation, electrochemistry is applied in a tin-mediated allylation reaction in water. In this electrochemical process, the corresponding homoallylic alcohols are prepared in excellent yields, while both tin salt and water can be recycled and electrode materials are not consumed.

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…Several years later, an aqueous-phase tin-mediated process was developed which utilizes graphite electrodes. 689 Electrogenerated zinc 690–692 and samarium(II) 609,693 could also facilitate such transformations. Additionally, Durandetti and co-workers reported an iron-catalyzed electrochemical allylation of carbonyl compounds by allylic acetates.…”

Electrochemical synthesis of 6-arylsulfonyl caffeic acid derivatives in aqueous medium

“…Organic electrochemical synthesis is another approach to green chemistry since many redox reagents are produced by electrochemical pathways, and thus eliminate the need for the waste disposal of a used redox reagent [4]. Therefore, the combination of organic synthesis in water and organic electrochemical synthesis can utilize advantages of both procedures and provide a more efficient approach to environmentally benign processes [5,6]. From this viewpoint, and because of the increasing environmental pressure, organic electrochemical synthesis in aqueous solution will become more and more attractive in the future.…”

Synthesis of homoallylic amines and acylhydrazides by tin powder‐promoted multicomponent one‐pot allylation reactions

“…Based on the experimental results and the literature, [31,51] a possible mechanism is tentatively proposed as shown in Scheme 4. Amines or N-acylhydrazines react with aldehydes or ketones firstly …”

“…Subsequently, allylations mediated by metallic tin were investigated in the presence of water or just using water as solvent, but most studies focused on allylation of aldehydes. [31,[51][52][53][54][55] Some other substrates such as nitroalkenes, [11] enol ethers [56] and aldoximes [57] were also allylated using allylic bromide and metallic tin in water to give homoallylic alcohols.…”