Manganese-catalyzed synthesis of polyketones using hydrogen-borrowing approach.

Kulyabin, Pavel S.; Magdysyuk, Oxana V.; Naden, Aaron B.; Dawson, Daniel M.; Pancholi, Ketan; Walker, Matthew; Vassalli, Massimo; Kumar, Amit

Abstract

We report here a method of making polyketones from the coupling of diketones and diols using a manganese pincer complex. The methodology allows us to access various polyketones (polyarylalkylketone) containing aryl, alkyl, and ether functionalities, bridging the gap between the two classes of commercially available polyketones: aliphatic polyketones and polyaryletherketones. Using this methodology, 12 polyketones have been synthesized and characterized using various analytical techniques to understand their chemical, physical, morphological, and mechanical properties. Based on previous reports and our studies, we suggest that the polymerization occurs via a hydrogen-borrowing mechanism that involves the dehydrogenation of diols to dialdehyde followed by aldol condensation of dialdehyde with diketones to form chalcone derivatives and their subsequent hydrogenation to form polyarylalkylketones.

Citation

KULYABIN, P.S., MAGDYSYUK, O.V., NADEN, A.B., DAWSON, D.M., PANCHOLI, K., WALKER, M., VASSALLI, M. and KUMAR, A. 2024. Manganese-catalyzed synthesis of polyketones using hydrogen-borrowing approach. ACS catalysis [online], 14(14), pages 10624-10634. Available from: https://doi.org/10.1021/acscatal.4c03019

• Journal Article Type: Article
• Acceptance Date: Jun 11, 2024
• Online Publication Date: Jun 28, 2024
• Publication Date: Jul 19, 2024
• Deposit Date: Jul 5, 2024
• Publicly Available Date: Jul 18, 2024
• Journal: ACS catalysis
• Electronic ISSN: 2155-5435
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 14
• Issue: 14
• Pages: 10624-10634
• DOI: https://doi.org/10.1021/acscatal.4c03019
• Keywords: Manganese; Polyketones; Diketones; Dehdrogenation; Hydrogen-borrowing
• Public URL: https://rgu-repository.worktribe.com/output/2403855
• Related Public URLs: https://rgu-repository.worktribe.com/output/2213035 (Preprint)