Jiao Z,
Jaunich KT,
Tao T,
Gottschall O,
Hughes MM,
Turlik A,
*,
Schuppe AW.
*
Vanderbilt University, Nashville and Skidmore College, Saratoga Springs, USA
Unified Approach to Deamination and Deoxygenation Through Isonitrile Hydrodecyanation: A Combined Experimental and Computational Investigation.
Angew. Chem. Int. Ed. 2024; e202405779
Key words
defunctionalization - hydrodecyanation - iridium photocatalysis - isonitriles - NHC boranes
Significance
Isonitriles, which are readily available from amines, alcohols, or alkenes, undergo a hydrodecyanation reaction under iridium photocatalysis. This protocol provides an alternative and facile way to defunctionalize alcohols and amines in two steps under mild reaction conditions.
Comment
This method is chemoselective for isonitriles in the presence of a nitrile group. However, if a heteroatom polarizes the C–CN bond, the protocol can be extended to nitriles (not shown). Density functional theory calculations support the observed reactivity pattern between the two functional groups.
