When it comes to the use of sodium hydride (NaH), the first reaction of many organic chemists is that it can be used to extract hydrogen. However, besides being a base, NaH can also be used as a nucleophile to attack electrophilic reagents. Recently, the research group of Professor Shunsuke Chiba of Nanyang Technological University in Singapore reported on Angew.chem.int.ed. the hydrogenation dehalogenation of halogenated aromatic hydrocarbons by NaH, in which iodide (MI, M = Li, Na) was used as additive (Scheme 1c).
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