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Visible-Light-Induced [2+2] cycloaddition of alkyne with alkene

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Title
Visible-Light-Induced [2+2] cycloaddition of alkyne with alkene
Author
Kwak, Yoonna
Advisor
Park, Cheol Min
Issue Date
2019-08
Publisher
Graduate School of UNIST
Abstract
All-carbon four-membered rings are important structural motifs because they can be found in numerous natural products. Also, they are useful intermediates for chemical synthesis due to their ring strain. The [2+2] cycloadditions are straightforward route to make the four-membered ring scaffold. However, there are disadvantages in terms of environmental impact due to the requirement of harsh condition such as UV light irradiation. Visible-light photocatalysis has emerged as a powerful tool for various organic synthesis because of its environmental strength. Visible-light irradiation is attractive because this reaction can tolerate sensitive functional groups that might be easily decomposed by UV irradiation. This strategy is mild and operationally simple reaction. Many variants using visible-light photocatalysis have been reported for significant transformations in organic synthesis. Visible-light-promoted [2+2] cycloadditions of alkene have also been vigorously developed. Nevertheless, the preparation of functionalized cyclobutenes still remains a challenge in contrast to cyclobutanes. Herein, we developed visible-light-induced [2+2] cycloaddition between alkyne and alkene. The visible-light-induced [2+2] photocycloaddition of alkyne with alkene was achieved via energy transfer mechanism. Using a blue LED as a light source and an iridium photocatalyst as a photosensitizer, a variety of cyclobutenes products were constructed in moderated to excellent yields. Also, conjugated diene products were directly accessed through [2+2] cycloaddition of enyne followed by ring-opening reaction. In contrast to previous examples of [2+2] photocycloadditions between alkyne and alkene, this strategy was achieved under visible-light irradiation. The resulting products are poised for various further modifications. Consequently, this method is expected to play an important role in the synthesis of complex organic molecules.
Description
Department of Chemistry
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