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Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis
Author(s) -
Köring Laura,
Sitte Nikolai A.,
Bursch Markus,
Grimme Stefan,
Paradies Jan
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100041
Subject(s) - frustrated lewis pair , catalysis , amide , chemistry , lewis acids and bases , catalytic hydrogenation , oxide , chloride , triphosgene , catalytic cycle , organic chemistry , metal , lewis acid catalysis , medicinal chemistry , phosgene
The metal‐free catalytic hydrogenation of secondary carboxylic acid amides is developed. The reduction is realized by two new catalytic reactions. First, the amide is converted into the imidoyl chloride by triphosgene (CO(OCCl 3 ) 2 ) using novel phosphorus(V) catalysts. Second, the in situ generated imidoyl chlorides are hydrogenated in high yields by an FLP‐catalyst. Mechanistic and quantum mechanical calculations support an autoinduced catalytic cycle for the hydrogenation with chloride acting as unusual Lewis base for FLP‐mediated H 2 ‐activation.