Regioselective Chromatic Orthogonality with Light-Activated Metathesis Catalysts

Angewandte Chemie
Efrat LevinN Gabriel Lemcoff

Abstract

The ability to selectively guide consecutive chemical processes towards a preferred pathway by using light of different frequencies is an appealing concept. Herein we describe the coupling of two photochemical reactions, one the photoisomerization and consequent activation of a sulfur-chelated latent olefin-metathesis catalyst at 350 nm, and the other the photocleavage of a silyl protecting group at 254 nm. Depending on the steric stress exerted by a photoremovable neighboring chemical substituent, we demonstrate the selective formation of either five- or six-membered-ring frameworks by light-triggered ring-closing metathesis. The orthogonality of these light-induced reactions allows the initiation of these processes independently and in interchangeable order, according to the wavelength of light used to promote them.

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Citations

Dec 19, 2015·PloS One·Karen S SarkisyanKonstantin A Lukyanov
Mar 24, 2016·Chemistry : a European Journal·Volodymyr Sashuk, Oksana Danylyuk
Feb 16, 2016·Beilstein Journal of Organic Chemistry·Ileana DragutanHelmut Fischer
Oct 2, 2020·Organic & Biomolecular Chemistry·Freya M Harvey, Christian G Bochet
May 7, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Or Eivgi, N Gabriel Lemcoff
Feb 13, 2021·Angewandte Chemie·Noy B NechmadN Gabriel Lemcoff
May 28, 2021·Angewandte Chemie·Danijela LunicChristopher J Teskey
Sep 30, 2020·Accounts of Chemical Research·Or EivgiN Gabriel Lemcoff
Dec 5, 2018·Inorganic Chemistry·Elisa IvryN Gabriel Lemcoff
Apr 24, 2019·Journal of the American Chemical Society·Cédric TheunissenTomislav Rovis

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