Journal
CHEMCATCHEM
Volume 12, Issue 14, Pages 3661-3665Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.202000260
Keywords
azides; dehydrogenation; iridium; nitriles; ruthenium
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Funding
- National Key R&D Program of China [2016YFA0202900]
- National Natural Science Foundation of China [21825109, 21821002, 21572255, 21732006]
- Chinese Academy of Sciences Key Research Program of Frontier Sciences [QYZDB-SSWSLH016]
- K.C.Wong Education Foundation
- Science and Technology Commission of Shanghai Municipality [17JC1401200]
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Pincer metal complexes exhibit superior catalytic activity in the dehydrogenation of plain alkanes, but find limited application in the dehydrogenation of functionalized organic molecules. Starting from easily accessible primary alkyl azides, here we report an efficient dehydrogenation of azides to nitriles using pincer iridium or ruthenium complexes as the catalysts. This method offers a route to cyanide-free preparation of nitriles without carbon chain elongation and without the use of strong oxidants. Both benzyl and linear aliphatic azides can be dehydrogenated with tert-butylethylene as the hydrogen acceptor to afford nitriles in moderate to high yields. Various functional groups can be tolerated, and the H-C-C-H bond dehydrogenation does not occur for linear alkyl azide substrates. Furthermore, the pincer Ir catalytic system was found to catalyze the direct azide dehydrogenation without the use of a sacrificial hydrogen acceptor.
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