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Catalyst‐Dependent Chemoselective Formal Insertion of Diazo Compounds into C−C or C−H Bonds of 1,3‐Dicarbonyl Compounds.
- Source :
-
Angewandte Chemie . 7/16/2018, Vol. 130 Issue 29, p9065-9069. 5p. - Publication Year :
- 2018
-
Abstract
- 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 catalyst, the reaction pathway switched to formal C−H insertion, affording 2‐alkylated 1,3‐dicarbonyl products. Different reaction pathways are proposed to account for this powerful catalyst‐dependent chemoselectivity. [ABSTRACT FROM AUTHOR]
- Subjects :
- *DIAZO compounds
*CHEMOSELECTIVITY
*SCANDIUM
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 130
- Issue :
- 29
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 130647086
- Full Text :
- https://doi.org/10.1002/ange.201802834