Carboxylic Acid Promoted, Redox‐Neutral Ru‐Catalyzed C−H Allylation of Aromatic Ketones

A redox‐neutral, carboxylic acid promoted, [RuCl2(p‐cymene)]2 catalyzed, weakly coordinating, carbonyl assisted C−H allylation of aromatic ketones has been developed. The beneficial effect of carboxylic acid on the ruthenium catalyst towards C−H allylation of aromatic ketones has been further explor...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2021-09, Vol.2021 (33), p.4611-4615
Main Authors: Dethe, Dattatraya H., Beeralingappa, Nagabhushana C., Dherange, Balu D.
Format: Article
Language:English
Subjects:
1-Adamantane carboxylic acid
Allyl compounds
Allylation
Aromatic ketones
Carbonyls
Carboxylic acids
Chemical reactions
Functional groups
Ketone directed reactions
Ketones
Ruthenium
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A redox‐neutral, carboxylic acid promoted, [RuCl2(p‐cymene)]2 catalyzed, weakly coordinating, carbonyl assisted C−H allylation of aromatic ketones has been developed. The beneficial effect of carboxylic acid on the ruthenium catalyst towards C−H allylation of aromatic ketones has been further explored, using commercially available allyl acetate under mild reaction conditions. In addition, this method requires redox‐neutral reaction conditions, easily accessible starting materials, and shows excellent functional group compatibility. An alternative method for the weakly coordinating, ketone‐directed C(sp2)−H allylation of aromatic ketones such as substituted acetophenones, 3‐acetyl indoles, and chalcones was developed under redox‐neutral conditions. 1‐Adamantane carboxylic acid plays a crucial role in improving the reactivity of the [RuCl2(p‐cymene)]2 catalyst at mild reaction temperatures. This method provides an access to various synthetically useful terminal olefin systems in moderate to good yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100717