Issue 40, 2023

Photocyclization by a triplet–triplet annihilation upconversion pair in water – avoiding UV-light and oxygen removal

Abstract

We present a formal [2 + 2]-cycloaddition of unsaturated ketones enabled by a green-to-ultraviolet triplet–triplet annihilation upconversion (TTA-UC) pair, using commercially available Ru(bpy)32+ and pyrene as sensitizer and annihilator, respectively. In the developed protocol, visible light irradiation at λmax = 520 nm allows for the reaction to proceed without the need for UV-light and the aqueous medium eliminates the need for oxygen removing protocols. Through this study, the application of the readily available upconversion pair is broadened to include cyclization reactions. We showcase the utility of the system by generating bicyclo[2.1.1]hexanes that are valuable bioisosteres of ortho-substituted benzenes, a promising motif for pharmaceuticals.

Graphical abstract: Photocyclization by a triplet–triplet annihilation upconversion pair in water – avoiding UV-light and oxygen removal

Supplementary files

Article information

Article type
Edge Article
Submitted
26 Jūn. 2023
Accepted
30 Aug. 2023
First published
31 Aug. 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 11040-11044

Photocyclization by a triplet–triplet annihilation upconversion pair in water – avoiding UV-light and oxygen removal

R. Jeyaseelan, M. Utikal, C. G. Daniliuc and L. Næsborg, Chem. Sci., 2023, 14, 11040 DOI: 10.1039/D3SC03242F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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