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

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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)9895-9901
Number of pages7
JournalChemical Science
Volume12
Issue number29
DOIs
Publication statusPublished - 7 Aug 2021

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