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Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds

A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds of aliphatic amides was demonstrated using atmospheric (1–2 atm) carbon monoxide as a C1 source. This straightforward approach provides access to α-spiral succinimide regioselectively in a good yield. C...

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Detalles Bibliográficos
Autores principales: Barsu, Nagaraju, Bolli, Shyam Kumar, Sundararaju, Basker
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369400/
https://www.ncbi.nlm.nih.gov/pubmed/28451350
http://dx.doi.org/10.1039/c6sc05026c
Descripción
Sumario:A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds of aliphatic amides was demonstrated using atmospheric (1–2 atm) carbon monoxide as a C1 source. This straightforward approach provides access to α-spiral succinimide regioselectively in a good yield. Cobalt catalyzed sp(3) C–H bond carbonylation is reported for the first time including the functionalization of (β)-C–H bonds of α-1°, 2°, 3° carbons and even internal (β)-C–H bonds. Our initial mechanistic investigation reveals that the C–H activation step is irreversible and will possibly be the rate determining step.