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DOI: 10.1055/s-0043-1773296
Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane
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.
Key words
defunctionalization - hydrodecyanation - iridium photocatalysis - isonitriles - NHC boranesSignificance
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.
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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.
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Publication History
Article published online:
14 June 2024
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