PDF herunterladen
Synfacts 2024; 20(07): 0705
DOI: 10.1055/s-0043-1773296
Metals in Synthesis

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Rezensent(en):
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
CrossrefPubMedSuche in Google Scholar
› Weitere Informationen
 als PDF herunterladen Lizenzen und Reprints

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.


#
#

Publikationsverlauf

Artikel online veröffentlicht:
14. Juni 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany