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Innovative industrial technology starts with iodine
Published in Tatsuo Kaiho, Iodine Made Simple, 2017
SmI2 is a strong reducing agent that reacts rapidly with water to produce hydrogen. In an organic reaction, it can reduce halides, ketones, esters, and sulfoxides. A typical SmI2 reaction is the Barbier reaction which produces tertiary alcohol from ketone and alkyl halide. There are reports on the intramolecular reaction producing a five-membered ring or a six-membered ring. Furthermore, pinacol coupling stereoselectively proceeds with a high yield [40b].
Atom Economy
Published in Aidé Sáenz-Galindo, Adali Oliva Castañeda-Facio, Raúl Rodríguez-Herrera, Green Chemistry and Applications, 2020
Kunnambeth M. Thulasi, Sindhu Thalappan Manikkoth, Manjacheri Kuppadakkath Ranjusha, Padinjare Veetil Salija, Nisha Vattakkoval, Shajesh Palantavida, Baiju Kizhakkekilikoodayil Vijayan
Fishback et al. in 2016 compared various reactions through a green approach. According to him, the Barbier reaction which is an aqueous version of the Grignard reaction, is less toxic and greener than the Grignard reaction, illustrated in Scheme 2.17. Unlike the Barbier reaction, the Grignard synthesis has to be performed in anhydrous condition in organic solvents. Atom economy of the Barbier reaction is 65%.
Density functional and ab initio study of samarium dihalides, SmX2 (X = I, Br, and Cl)
Published in Molecular Physics, 2019
Jiwon Moon, Heehyun Baek, Joonghan Kim
Samarium diiodide (SmI2) is a well-known one-electron reducing agent that is popularly used in the Barbier reaction [1]. SmI2 is especially useful for the formation of C–C bond in total synthesis [2]. In addition, SmI2 generate a radical intermediate that undergoes addition to an alkene or alkyne [1,2]. These organic reactions involving the participation of SmI2 have been reviewed many times in the literature [1-7]. However, despite the importance and usefulness of SmI2, a detailed theoretical investigation of SmI2 in the gas phase has not yet been performed.