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Rh(DPEPhos)-catalyzed alkyne hydroacylation using β-carbonyl-substituted aldehydes: mechanistic insight leads to low catalyst loadings that enables selective catalysis on gram-scale

Abstract:

The detailed mechanism of the hydroacylation of β-amido-aldehyde, 2,2-dimethyl-3-morpholino-3-oxopropanal, with 1-octyne using [Rh(cis-κ2-P,P-DPEPhos)(acetone)2][BArF4]-based catalysts, is described [ArF = (CF3)2C6H3]. A rich mechanistic landscape of competing and interconnected hydroacylation and cyclotrimerization processes is revealed. An acyl-hydride complex, arising from oxidative addition of aldehyde, is the persistent resting state during hydroacylation, and quaternary substitution at ...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1021/jacs.8b04086

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Inorganic Chemistry
Oxford college:
Magdalen College
ORCID:
0000-0003-1646-8081
Publisher:
American Chemical Society Publisher's website
Journal:
Journal of the American Chemical Society Journal website
Volume:
140
Issue:
23
Pages:
7347–7357
Publication date:
2018-05-15
Acceptance date:
2018-05-15
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Pubs id:
pubs:847828
URN:
uri:b04bb249-1811-4235-8148-0fa7b565e901
UUID:
uuid:b04bb249-1811-4235-8148-0fa7b565e901
Local pid:
pubs:847828

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