Journal
CATALYSIS SCIENCE & TECHNOLOGY
Volume 9, Issue 17, Pages 4711-4717Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cy01231a
Keywords
-
Categories
Funding
- China Scholarship Council
- COST Action (CHAOS) [CA15106]
Ask authors/readers for more resources
The first use of biologically relevant isoindolinones as weak directing groups in transition metal-catalyzed carbon-carbon bond formation via C-H bond functionalization is presented. Notably, besides the presence of two aromatic C-H sites available for functionalization, selective mono-alkenylation in the ortho-position with respect to the nitrogen atom were achieved with a readily available ruthenium catalyst. The scalability, versatility and high functional group tolerance of the catalysis enabled the late-stage functionalization of biologically relevant indoprofen and further derivatizations. Preliminary mechanistic studies indicate (1) the ease of the C-H bond activation step, (2) the key role of the carbonyl group as a weak directing group throughout the catalytic cycle and (3) the unexpected subtle differences associated between cyclic amides and imides as weak directing groups in ruthenium-catalyzed C-H bond alkenylation reactions. The isolation and role of an unprecedented off-cycle ruthenium complex is discussed as well.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available