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Catalyst-dependent chemoselective formal insertion of diazo compounds into C-C or C-H bonds of 1,3-dicarbonyl compounds

Abstract:

A catalyst‐dependent chemoselective one‐carbon insertion of diazo compounds into the C−C or C−H bonds of 1,3‐dicarbonyl species is reported. In the presence of silver(I) triflate, diazo insertion into the C(=O)−C bond of the 1,3‐dicarbonyl substrate leads to a 1,4‐dicarbonyl product containing an all‐carbon α‐quaternary center. This reaction constitutes the first example of an insertion of diazo‐derived carbenoids into acyclic C−C bonds. When instead scandium(III) triflate was applied as the ...

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

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Files:
Publisher copy:
10.1002/anie.201802834

Authors


Sivaguru, P More by this author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
Jesus College
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie International Edition Journal website
Volume:
57
Issue:
29
Pages:
8927-8931
Publication date:
2018-05-08
Acceptance date:
2018-05-07
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Pubs id:
pubs:847948
URN:
uri:81a839fd-f890-4b17-bb6e-48ea53f4bcdf
UUID:
uuid:81a839fd-f890-4b17-bb6e-48ea53f4bcdf
Local pid:
pubs:847948

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