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Cobalt catalyzed carbonylation of unactivated C(sp³)-H bonds.

ABSTRACT: A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp³)-H bonds of aliphatic amides was demonstrated using atmospheric (1-2 atm) carbon monoxide as a C1 source. This straightforward approach provides access to ?-spiral succinimide regioselectively in a good yield. Cobalt catalyzed sp³ C-H bond carbonylation is reported for the first time including the functionalization of (?)-C-H bonds of ?-1°, 2°, 3° carbons and even internal (?)-C-H bonds. Our initial mechanistic investigation reveals that the C-H activation step is irreversible and will possibly be the rate determining step.

SUBMITTER: Barsu N

PROVIDER: S-EPMC5369400 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Cobalt catalyzed carbonylation of unactivated C(sp3)-H bonds.

Barsu Nagaraju N Bolli Shyam Kumar SK Sundararaju Basker B

Chemical science 20161220 3

A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp3)-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 sp3 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. ...[more]

PMID: 28451350

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