ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1

Tropolonate Salts as Acyl Transfer Catalysts for Esterification Reactions under Thermal and Photochemical Conditions

preprint
submitted on 19.08.2020 and posted on 20.08.2020 by Demelza Lyons, Claire Empel, Domenic Pace, An Huy Dinh, Binh Khanh Mai, Rene Koenigs, Thanh Vinh Nguyen
Acyl transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl transfer reaction. Herein we introduce a new acyl transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give the products with excellent efficiency under thermal or blue light-photochemical conditions. Kinetic studies and density functional theory (DFT) calculations suggest interesting mechanistic insights for reactions promoted by this new acyl transfer catalytic system.

Funding

Novel organic architectures and functional materials from tropylium ions

Australian Research Council

Find out more...

Organic Linchpin Reagents to Construct Structural Diversity and Complexity

Australian Research Council

Find out more...

History

Email Address of Submitting Author

t.v.nguyen@unsw.edu.au

Institution

University of New South Wales, Sydney

Country

Australia

ORCID For Submitting Author

0000-0002-0757-9970

Declaration of Conflict of Interest

No conflict of interest to declare.

Exports