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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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
Terminals
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creator Ostrowski, Karoline A.
Faßbach, Thiemo A.
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description 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.
doi_str_mv 10.1002/adsc.201401031
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subjects Bonding
carbenes
Catalysis
Conversion
high-pressure chemistry
homogeneous catalysis
hydroformylation
Ketones
Olefins
organocatalysis
Rhodium
Synthesis
Terminals
title Tandem Hydroformylation/Acyloin Reaction - The Synergy of Metal Catalysis and Organocatalysis Yielding Acyloins Directly from Olefins
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