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Catalytic hydrogen atom transfer from hydrosilanes to vinylarenes for hydrosilylation and polymerization
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2019 (English)In: Nature Catalysis, ISSN 2520-1158, Vol. 2, no 2, p. 164-173Article in journal (Refereed) Published
Abstract [en]

Because of the importance of hydrogen atom transfer (HAT) in biology and chemistry, there is increased interest in new strategies to perform HAT in a sustainable manner. Here, we describe a sustainable, net redox-neutral HAT process involving hydrosilanes and alkali metal Lewis base catalysts-eliminating the use of transition metal catalysts-and report an associated mechanism concerning Lewis base-catalysed, complexation-induced HAT. The catalytic Lewis base-catalysed, complexation-induced HAT is capable of accessing both branch-specific hydrosilylation and polymerization of vinylarenes in a highly selective fashion, depending on the Lewis base catalyst used. In this process, the Earth-abundant, alkali metal Lewis base catalyst plays a dual role. It first serves as a HAT initiator and subsequently functions as a silyl radical stabilizing group, which is critical to highly selective cross-radical coupling. An electron paramagnetic resonance study identified a potassiated paramagnetic species, and multistate density functional theory revealed a high HAT character, yet multiconfigurational nature in the transition state of the reaction.

Place, publisher, year, edition, pages
Nature Publishing Group, 2019. Vol. 2, no 2, p. 164-173
National Category
Organic Chemistry
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URN: urn:nbn:se:umu:diva-156880DOI: 10.1038/s41929-018-0217-zISI: 000458554800012OAI: oai:DiVA.org:umu-156880DiVA, id: diva2:1295259
Available from: 2019-03-11 Created: 2019-03-11 Last updated: 2019-03-11Bibliographically approved

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Nam, Kwangho

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