Discovery of a photochemical cascade process by flow-based interception of isomerising alkenes

Di Filippo, Mara; Trujillo, Cristina; Sánchez-Sanz, Goar; Batsanov, Andrei S.; Baumann, Marcus

Abstract

Herein we report the discovery of a new photochemical cascade process through a flow-based strategy for intercepting diradicals generated from simple alkenes. This continuous process delivers a series of unprecedented polycyclic reaction products. Exploring the scope of this novel process revealed that this approach is general and affords a variety of structurally complex reaction products in high yields (up to 81%), short reaction times (7 min) and high throughputs (up to 5.5 mmol h−1). A mechanistic rationale is presented that is supported by computations as well as isolation of key intermediates whose identity is confirmed by X-ray crystallography. The presented photochemical cascade process demonstrates the discovery of new chemical reactivity and complex chemical scaffolds by continuously generating and intercepting high-energy intermediates in a highly practical manner.

Citation

Di Filippo, M., Trujillo, C., Sánchez-Sanz, G., Batsanov, A. S., & Baumann, M. (2021). Discovery of a photochemical cascade process by flow-based interception of isomerising alkenes. Chemical Science, 12(29), https://doi.org/10.1039/d1sc02879k

• Journal Article Type: Article
• Acceptance Date: Jul 2, 2021
• Online Publication Date: Jul 5, 2021
• Publication Date: 2021
• Deposit Date: Nov 16, 2021
• Publicly Available Date: Nov 16, 2021
• Journal: Chemical Science
• Print ISSN: 2041-6520
• Electronic ISSN: 2041-6539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 12
• Issue: 29
• DOI: https://doi.org/10.1039/d1sc02879k
• Public URL: https://durham-repository.worktribe.com/output/1221640