Copper-Catalyzed Decarboxylative Radical Silylation of Redox-Active Aliphatic Carboxylic Acid Derivatives.
Angew Chem Int Ed Engl
; 56(38): 11649-11652, 2017 09 11.
Article
en En
| MEDLINE
| ID: mdl-28742250
ABSTRACT
A decarboxylative silylation of aliphatic N-hydroxyphthalimide (NHPI) esters using Si-B reagents as silicon pronucleophiles is reported. This C(sp3 )-Si cross-coupling is catalyzed by copper(I) and follows a radical mechanism, even with exclusion of light. Both primary and secondary alkyl groups couple effectively, whereas tertiary alkyl groups are probably too sterically hindered. The functional-group tolerance is generally excellent, and α-heteroatom-substituted substrates also participate well. This enables, for example, the synthesis of α-silylated amines starting from NHPI esters derived from α-amino acids. The new method extends the still limited number of C(sp3 )-Si cross-couplings of unactivated alkyl electrophiles.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2017
Tipo del documento:
Article
País de afiliación:
Alemania