199166-26-2Relevant articles and documents
Novel Zn/ZnI2-promoted cross-coupling of acrylic acid esters with arylaldehydes to α-aroyladipic acid esters
Sakurai, Hidehiro,Takeuchi, Hiroki,Hirao, Toshikazu
, p. 3048 - 3049 (2002)
Cross-coupling of alkyl acrylates and arylaldehydes was achieved by treatment with metallic zinc and zinc(II) iodide in DMF, giving dialkyl α-aroyladipates in moderate yields.
Electrochemical Arylation of Aldehydes, Ketones, and Alcohols: from Cathodic Reduction to Convergent Paired Electrolysis
Zhang, Sheng,Li, Lijun,Li, Jingjing,Shi, Jianxue,Xu, Kun,Gao, Wenchao,Zong, Luyi,Li, Guigen,Findlater, Michael
supporting information, p. 7275 - 7282 (2021/03/01)
Arylation of carbonyls, one of the most common approaches toward alcohols, has received tremendous attention, as alcohols are important feedstocks and building blocks in organic synthesis. Despite great progress, there is still a great gap to develop an ideal arylation method featuring mild conditions, good functional group tolerance, and readily available starting materials. We now show that electrochemical arylation can fill the gap. By taking advantage of synthetic electrochemistry, commercially available aldehydes (ketones) and benzylic alcohols can be readily arylated to provide a general and scalable access to structurally diverse alcohols (97 examples, >10 gram-scale). More importantly, convergent paired electrolysis, the ideal but challenging electrochemical technology, was employed to transform low-value alcohols into more useful alcohols. Detailed mechanism study suggests that two plausible pathways are involved in the redox neutral α-arylation of benzylic alcohols.
Photocatalytic pinacol C-C coupling and jet fuel precursor production on ZnIn2S4nanosheets
Cao, Zhi,Han, Guanqun,Liu, Xingwu,Sun, Yujie
, p. 9346 - 9355 (2020/10/09)
Visible light-driven C-C bond formation has attracted increasing attention recently, thanks to the advance in molecular photosensitizers and organometallic catalysts. Nevertheless, these homogeneous methodologies typically necessitate the utilization of noble metal-based (e.g., Ir, Ru, etc.) photosensitizers. In contrast, solid-state semiconductors represent an attractive alternative but remain less explored for C-C bond-forming reactions driven by visible-light irradiation. Herein, we report that photocatalytic pinacol C-C coupling of benzaldehyde to hydrobenzoin can be achieved on two-dimensional ZnIn2S4 nanosheets upon visible-light irradiation in the presence of a sacrificial electron donor (e.g., triethylamine). We further demonstrate that it is feasible to take advantage of both excited electrons and holes in irradiated ZnIn2S4 for C-C coupling reactions in the absence of any sacrificial reagent if benzyl alcohol is utilized as the starting substrate, maximizing the energy efficiency of photocatalysis and circumventing any byproducts. In this case, industrially important benzoin and deoxybenzoin are formed as the final products. More importantly, by judiciously tuning the photocatalytic conditions, we are able to produce either benzoin or deoxybenzoin with unprecedented high selectivity. The critical species during the photocatalytic process were systematically investigated with various scavengers. Finally, such a heterogeneous photocatalytic pinacol C-C coupling strategy was applied to produce a jet fuel precursor (e.g., hydrofuroin) from biomass-derived furanics (e.g., furfural and furfural alcohol), highlighting the promise of our approach in practical applications.
