Issue 73, 2020

Palladium-catalyzed ortho-halogen-induced deoxygenative approach of alkyl aryl ketones to 2-vinylbenzoic acids

Abstract

The 2-vinylbenzoic acids have wide applications in the field of polymer chemistry and are key precursors for the synthesis of important bioactive molecules. Herein, an ortho-halogen-induced deoxygenative approach for the generation of 2-vinylbenzoic acids from alkyl aryl ketones by palladium catalysis is discovered and explored. This approach requires no base or stoichiometric additives and can be carried out through a simple one-step process. Furthermore, the present reaction is scalable up to one-gram scale. The commercially available palladium on carbon (5 wt%) was used as a heterogeneous catalyst and showed excellent recyclability (<5 times) without significant loss in catalytic activity. Pleasingly, under our optimized conditions, the alpha alkyl substituted 2-iodoacetophenones exhibit good diastereoselectivity and predominantly (E)-2-vinylbenzoic acids were obtained with good to excellent yields.

Graphical abstract: Palladium-catalyzed ortho-halogen-induced deoxygenative approach of alkyl aryl ketones to 2-vinylbenzoic acids

Supplementary files

Article information

Article type
Communication
Submitted
23 Apr 2020
Accepted
23 Jul 2020
First published
24 Jul 2020

Chem. Commun., 2020,56, 10674-10677

Palladium-catalyzed ortho-halogen-induced deoxygenative approach of alkyl aryl ketones to 2-vinylbenzoic acids

S. Ram, A. K. Sharma, A. S. Chauhan and P. Das, Chem. Commun., 2020, 56, 10674 DOI: 10.1039/D0CC02941F

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