Platinum(II)-Catalyzed Allylation of CO and CN Bonds under Hydrogenation Conditions

The nucleophilic addition of allylplatinum to a range of electrophiles including carbonyls, oximes, and hydrazones was examined. Platinum(II) catalysts and allene substrates were subject to hydrogenation conditions to generate nucleophilic allylplatinum complexes without using a stoichiometric amoun...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2010-11, Vol.352 (17), p.2949-2954
Main Authors: Hong, Jong-Tai, Wang, Xi, Kim, Ji-Hwan, Kim, Kyunghee, Yun, Hoseop, Jang, Hye-Young
Format: Article
Language:English
Subjects:
allylation
cyclization
hydrazones
hydrogenation
platinum
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Summary:The nucleophilic addition of allylplatinum to a range of electrophiles including carbonyls, oximes, and hydrazones was examined. Platinum(II) catalysts and allene substrates were subject to hydrogenation conditions to generate nucleophilic allylplatinum complexes without using a stoichiometric amount of toxic and sensitive organometallic reagents. The allylplatinum intermediates reacted with CO and CN bonds to produce the corresponding homoallylic alcohol and amine derivatives in good yield. The Pt‐catalyzed allylation of CN bonds is the first example performed under hydrogenation conditions. A reaction mechanism initiated with the hydrometalation of allenes by PtH species is proposed based on deuterium labeling studies.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201000648