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Ag-Catalyzed Insertion of Alkynyl Carbenes into C-C Bonds of β-Ketocarbonyls: A Formal C(sp 2 ) Insertion.
- Source :
-
Organic letters [Org Lett] 2022 Jan 21; Vol. 24 (2), pp. 631-636. Date of Electronic Publication: 2022 Jan 05. - Publication Year :
- 2022
-
Abstract
- Here we report a silver-catalyzed alkynyl carbene insertion into β-ketocarbonyls using alkynyl N -nosylhydrazones as alkynyl carbene precursors, which provides access to trisubstituted allenyl ketones. This reaction represents the first example of an alkynyl carbene insertion into a C-C σ bond, affording products homologated with an sp <superscript>2</superscript> carbon center. The products are useful substrates for further transformations. Experimental investigations and theoretical calculations suggest the reaction proceeds through a stepwise enol cyclopropanation/retro-aldol pathway.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 24
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 34985288
- Full Text :
- https://doi.org/10.1021/acs.orglett.1c04081