Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Martin Oestreich; Hendrik F. T. Klare; Emilio Acuña Bolomey

doi:10.1055/s-0043-1773296

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Synfacts 2024; 20(07): 0705
DOI: 10.1055/s-0043-1773296

Metals in Synthesis

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Contributor(s):

Martin Oestreich

,

Hendrik F. T. Klare

,

Emilio Acuña Bolomey

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
DOI: 10.1002/anie.202405779

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Abstract
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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.

Publication History

Article published online:
14 June 2024

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

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