Tandem Hydroformylation/Acyloin Reaction - The Synergy of Metal Catalysis and Organocatalysis Yielding Acyloins Directly from Olefins

A novel, atom efficient, orthogonal tandem catalysis was developed yielding acyloin products (α‐hydroxy ketones) directly from olefins under hydroformylation conditions. The combination of a metal‐catalysed hydroformylation and an organocatalysed acyloin reaction provides three atom efficient CC bo...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-05, Vol.357 (7), p.1374-1380
Main Authors: Ostrowski, Karoline A., Faßbach, Thiemo A., Vorholt, Andreas J.
Format: Article
Language:English
Subjects:
Bonding
carbenes
Catalysis
Conversion
high-pressure chemistry
homogeneous catalysis
hydroformylation
Ketones
Olefins
organocatalysis
Rhodium
Synthesis
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Summary:A novel, atom efficient, orthogonal tandem catalysis was developed yielding acyloin products (α‐hydroxy ketones) directly from olefins under hydroformylation conditions. The combination of a metal‐catalysed hydroformylation and an organocatalysed acyloin reaction provides three atom efficient CC bond formations to linear, multifunctional molecules via linkage of the intermediate n‐aldehydes. Additionally, the rhodium catalyst system gives a high n/bra ratio with an exclusive conversion of the terminal double bond in the hydroformylation and the n‐aldehydes are converted selectively to their acyloins.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201401031