Silyl Esters as Reactive Intermediates in Organic Synthesis

Adler, Marc J.; D’Amaral, Melissa C.; Andrews, Keith G.; Denton, Ross

Abstract

Silyl esters have been exploited as metastable reaction intermediates, both purposefully and unintentionally, since at least the 1960s. Their reactivity is broadly related to the substituents on the silicon, and in this way their properties can be readily modulated. Silyl esters have unique reactivity profiles that have been used to generate downstream products of a range of functionalities, and because of this many excellent methods for the synthesis of a variety of value-added chemicals have been developed. Furthermore, because of the frequent use of hydrosilanes as terminal reductants in catalytic processes, silyl ester intermediates are likely more commonly utilized by synthetic chemists than currently realized. This review comprehensively summarizes the reactions known to take advantage of reactive silyl ester intermediates and discusses examples of catalytic reactions that proceed in an unanticipated manner through silyl ester intermediates.

Citation

Adler, M. J., D’Amaral, M. C., Andrews, K. G., & Denton, R. (2023). Silyl Esters as Reactive Intermediates in Organic Synthesis. Synthesis: Journal of Synthetic Organic Chemistry, 55(20), 3209-3238. https://doi.org/10.1055/a-2083-8591

• Journal Article Type: Article
• Acceptance Date: Apr 28, 2023
• Online Publication Date: Jun 26, 2023
• Publication Date: 2023-10
• Deposit Date: May 14, 2024
• Journal: Synthesis
• Print ISSN: 0039-7881
• Electronic ISSN: 1437-210X
• Publisher: Thieme Gruppe
• Peer Reviewed: Peer Reviewed
• Volume: 55
• Issue: 20
• Pages: 3209-3238
• DOI: https://doi.org/10.1055/a-2083-8591
• Public URL: https://durham-repository.worktribe.com/output/2438984