95091-92-2Relevant articles and documents
Synthesis of [2,2’]Bifuranyl-5,5’-dicarboxylic Acid Esters via Reductive Homocoupling of 5-Bromofuran-2-carboxylates Using Alcohols as Reductants?
Jiang, Huanfeng,Luo, Jiajun,Xie, Yi,Yin, Biaolin,Yu, Bin
, p. 62 - 68 (2020/12/09)
Herein, we describe an environmentally benign and cost-effective protocol for the synthesis of valuable bifuranyl dicarboxylates, starting with α-bromination of readily accessible furan-2-carboxylates by LiBr and K2S2O8. Furthermore, the bromination intermediate product 5-bromofuran-2-carboxylates were then conducted in a palladium-catalyzed reductive homocoupling reactions in the presence of alcohols to afford bifuranyl dicarboxylates. One of the final products in this protocol, [2,2’]bifuran-5,5’-dicarboxylic acid esters, are essential monomers of poly(ethylene bifuranoate), which can be served as an green and versatile alternative polymer for traditional poly(ethylene terephthalate) that is currently common in technical plastics.
Selective Synthesis of Z-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones
Guven, Sinem,Kundu, Gourab,Rissanen, Kari,Schoenebeck, Franziska,Ward, Jas S.,We?els, Andrea
supporting information, p. 8375 - 8380 (2021/06/27)
We report a remote functionalization strategy, which allows the Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. The positional selectivity is controlled by the directionality of the chain walk and is independent of thermodynamic preferences of the resulting silyl enol ether. Our mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which serves as a catalyst resting state and, upon reaction with an alkyl bromide, is converted to [Ni(II)-H] as an active chain-walking/functionalization catalyst, ultimately generating a stabilized η3-bound Ni(II) enolate as the key selectivity-controlling intermediate.
Direct Alkoxycarbonylation of Heteroarenes via Cu-Mediated Trichloromethylation and in Situ Alcoholysis
Jiang, Huanfeng,Jiang, Kai,Li, Yingwei,Luo, Wenkun,Yin, Biaolin
supporting information, (2020/03/04)
We report an efficient approach for direct alkoxycarbonylation of furans as well as other heteroarenes via a one-step copper-mediated reaction of three components (i.e., heteroarene, alcohol, and CHCl3). The copper additive was confirmed to simultaneously promote the reaction in three pathways: oxidant cracking, single electron transfer, and alcoholysis. By means of this protocol, various functionalized furancarboxylates and other heteroarenecarboxylates were facilely obtained in moderate to good yields.