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분자활성 촉매반응 연구단
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Bronsted acid catalysis of photosensitized cycloadditions

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Title
Bronsted acid catalysis of photosensitized cycloadditions
Author(s)
Evan M. Sherbrook; Hoimin Jung; Dasol Cho; My-Hyun Baik; Tehshik P. Yoon
Publication Date
2020-01
Journal
CHEMICAL SCIENCE, v.11, no.3, pp.856 - 861
Publisher
ROYAL SOC CHEMISTRY
Abstract
Catalysis is central to contemporary synthetic chemistry. There has been a recent recognition that the rates of photochemical reactions can be profoundly impacted by the use of Lewis acid catalysts and co-catalysts. Herein, we show that Bronsted acids can also modulate the reactivity of excited-state organic reactions. Bronsted acids dramatically increase the rate of Ru(bpy)(3)(2+)-sensitized [2 + 2] photocycloadditions between C-cinnamoyl imidazoles and a range of electron-rich alkene reaction partners. A combination of experimental and computational studies supports a mechanism in which the Bronsted acid co-catalyst accelerates triplet energy transfer from the excited-state [Ru*(bpy)(3)](2+) chromophore to the Bronsted acid activated C-cinnamoyl imidazole. Computational evidence further suggests the importance of driving force as well as geometrical reorganization, in which the protonation of the imidazole decreases the reorganization penalty during the energy transfer event. © The Royal Society of Chemistry 2020
URI
https://pr.ibs.re.kr/handle/8788114/7044
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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