peri‐xanthenoxanthene (PXX): a versatile organic photocatalyst in organic synthesis

Pezzetta, Cristofer, Folli, Andrea ORCID: https://orcid.org/0000-0001-8913-6606, Matuszewska, Oliwia, Murphy, Damien ORCID: https://orcid.org/0000-0002-5941-4879, Davidson, Robert W. M. and Bonifazi, Davide ORCID: https://orcid.org/0000-0001-5717-0121 2021. peri‐xanthenoxanthene (PXX): a versatile organic photocatalyst in organic synthesis. Advanced Synthesis and Catalysis 363 (20) , pp. 4740-4753. 10.1002/adsc.202100030

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Abstract

Recent years have witnessed a continuous development of photocatalysts to satisfy the growing demand of photophysical and redox properties in photoredox catalysis, with complex structures or alternative strategies devised to access highly reducing or oxidising systems. We report herein the use of peri‐xanthenoxanthene (PXX), a simple and inexpensive dye, as an efficient photocatalyst. Its highly reducing excited state allows activation of a wide range of substrates, thus triggering useful radical reactions. Benchmark transformations such as the addition of organic radicals, generated by photoreduction of organic halides, to radical traps are initially demonstrated. More complex dual catalytic manifolds are also shown to be accessible: the β‐arylation of cyclic ketones is successful when using a secondary amine as organocatalyst, while cross‐coupling reactions of aryl halides with amines and thiols are obtained when using a Ni co‐catalyst. Application to the efficient two‐step synthesis of the expensive fluoro‐tetrahydro‐1H‐pyrido[4,3‐b]indole, a crucial synthetic intermediate for the investigational drug setipiprant, has been also demonstrated.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Additional Information:	This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License
Publisher:	Wiley
ISSN:	1615-4150
Date of First Compliant Deposit:	14 April 2021
Date of Acceptance:	19 March 2021
Last Modified:	06 Jan 2024 04:44
URI:	https://orca.cardiff.ac.uk/id/eprint/140458

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