title: Hydride Reduction by a Sodium Hydride-Iodide Composite.
abstract: Sodium hydride (NaH) is widely used as a Brønsted base in chemical synthesis and reacts with various Brønsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with unprecedented and unique hydride-donor chemical reactivity.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
authors.forename: Pei Chui
authors.initials: PC
authors.lastname: Too
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
authors.forename: Guo Hao
authors.initials: GH
authors.lastname: Chan
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
authors.forename: Ya Lin
authors.initials: YL
authors.lastname: Tnay
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore. hirao@ntu.edu.sg.
authors.forename: Hajime
authors.initials: H
authors.lastname: Hirao
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore. shunsuke@ntu.edu.sg.
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Chiba
keywords: amides; decyanation; density functional calculations; reduction; sodium hydride