Regioselective Chromatic Orthogonality with Light-Activated Metathesis Catalysts

Autor: Or Eivgi, Efrat Levin, N. Gabriel Lemcoff, Sudheendran Mavila, Eyal Tzur
Rok vydání: 2015
Předmět:
Zdroj: Angewandte Chemie. 127:12561-12565
ISSN: 0044-8249
DOI: 10.1002/ange.201500740
Popis: 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.
Databáze: OpenAIRE