Photosensitized selective semi-oxidation of tetrahydroisoquinoline: a singlet oxygen path

Yaghmaei, Mahzad; Villanueva, Martin; Martín-García, Iris; Alonso, Francisco; Zhang, Xiaocong; Joshi, Neeraj; Lanterna, Anabel E.; Scaiano, Juan C.

Abstract

Selective semi-oxidation of tetrahydroisoquinoline (THIQ) leads to a valuable dihydroisoquinoline (DHIQ) derivative via singlet oxygen photooxidation process. Typical photosensitisers (i.e., Ru complexes) can activate the reaction even under heterogeneous conditions that facilitate catalyst separation and reusability. In contrast to DHIQ, THIQ acts as an efficient singlet oxygen quencher driving the reaction selectivity. The reaction can also be facilitated by semiconductor catalysts such as MoCo@GW, a glass wool-based catalyst that is easy to separate and reuse and compatible with flow photochemistry. Its role is to mediate the formation of isoquinoline (IQ) and thus an in situ-generated singlet oxygen catalyst. Laser flash photolysis with NIR detection provides proof of the singlet oxygen mechanism proposed and rate constants for the key steps that mediate the oxidation.

Citation

Yaghmaei, M., Villanueva, M., Martín-García, I., Alonso, F., Zhang, X., Joshi, N., Lanterna, A. E., & Scaiano, J. C. (2022). Photosensitized selective semi-oxidation of tetrahydroisoquinoline: a singlet oxygen path. Photochemical & Photobiological Sciences, 21(8), 1473-1479. https://doi.org/10.1007/s43630-022-00237-9

• Journal Article Type: Article
• Acceptance Date: Apr 22, 2022
• Online Publication Date: May 18, 2022
• Publication Date: 2022-08
• Deposit Date: May 24, 2022
• Publicly Available Date: May 19, 2023
• Journal: Photochemical & Photobiological Sciences
• Print ISSN: 1474-905X
• Electronic ISSN: 1474-9092
• Publisher: Springer
• Peer Reviewed: Peer Reviewed
• Volume: 21
• Issue: 8
• Pages: 1473-1479
• DOI: https://doi.org/10.1007/s43630-022-00237-9
• Keywords: Photochemistry
• Public URL: https://nottingham-repository.worktribe.com/output/8219549
• Publisher URL: https://link.springer.com/article/10.1007/s43630-022-00237-9
• Additional Information: This version of the article has been accepted for publication, after peer review (when applicable) and is not the Version of Record and does not reflect post-acceptance improvements, or any corrections. The Version of Record is available online at: https://dx.doi.org/10.1007/s43630-022-00237-9