90005537

open access

Accepted Manuscript

Photoinduced Nitrile Formation from O-(Arylcarbonyl) oxime: Usage as a Photoremovable Protecting Group

English (英語)

Chemphotochem

2(12)

1012-1016

Wiley-VCH Verlag

2018-12

2020-01-01

Employing a photoremovable protecting group is a useful technique to achieve precise conditional control over a biological function. This Communication reports the development of a photoremovable protecting group for the nitrile moiety. In the process, O-(arylcarbonyl) oxime was photochemically converted into the corresponding nitrile in the presence of a carbazole photosensitizer by means of an electron transfer from the excited carbazole to the arylcarbonyl unit. A variety of alkyl and (hetero) aryl nitriles were generated from the corresponding O-(arylcarbonyl) oximes. Moreover, a self-contained variant, in which O-(arylcarbonyl) oxime and carbazole units were covalently bonded, exhibited photochemical nitrile formation even in a highly diluted aqueous solution (0.1 mM), thus demonstrating that this molecular motif is potentially applicable in biological systems.

radicals

学術雑誌論文

© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer-reviewed version of the following article: [Chemphotochem, 2(12):1012-1016, 2018], which has been published in final form at https://doi.org/10.1002/cptc.201800167. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.