Multicomponent Oxyalkylation of Styrenes Enabled by Hydrogen-Bond-Assisted Photoinduced Electron Transfer
Adrian Tlahuext-Aca1, R Aleyda Garza-Sanchez1, Frank Glorius1
1NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, 48149, Münster, Germany.
Abstract:
Herein, we disclose a strategy for the activation of N-(acyloxy)phthalimides towards photoinduced electron transfer through hydrogen bonding. This activation mode enables efficient access to C(sp3 )-centered radicals upon decarboxylation from bench-stable and readily available substrates. Moreover, we demonstrate that the formed alkyl radicals can be successfully employed in a novel redox-neutral method for constructing sp3 -sp3 bonds across styrene moieties that gives straightforward access to complex alcohol and ether scaffolds.
Related Concept Videos
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Hydroboration-Oxidation of Alkenes
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
Radical Anti-Markovnikov Addition to Alkenes: Overview
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide


