Issue 3, 2017

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 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. Our initial mechanistic investigation reveals that the C–H activation step is irreversible and will possibly be the rate determining step.

Graphical abstract: Cobalt catalyzed carbonylation of unactivated C(sp3)–H bonds

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Nov 2016
Accepted
19 Dec 2016
First published
20 Dec 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 2431-2435

Cobalt catalyzed carbonylation of unactivated C(sp3)–H bonds

N. Barsu, S. K. Bolli and B. Sundararaju, Chem. Sci., 2017, 8, 2431 DOI: 10.1039/C6SC05026C

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