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Alkenes as alkyne equivalents in radical cascades terminated by fragmentations

Title: Alkenes as alkyne equivalents in radical cascades terminated by fragmentations.
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Name(s): Alabugin, Igor V., inventor
Mondal, Sayantan, inventor
Mohamed, Rana K., inventor
Type of Resource: text
Genre: Utility
Text
Date Created: 2016-05-02
Date Issued: 2017-07-18
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: Disclosed are methods for rerouting radical cascade cyclizations by using alkenes as alkyne equivalents. The reaction sequence is initiated by a novel 1,2 stannyl shift which achieves chemo- and regioselectivity in the process. The radical “hopping” leads to the formation of the radical center necessary for the sequence of selective cyclizations and fragmentations to follow. In the last step of the cascade, the elimination of a rationally designed radical leaving group via β-C—C bond scission aromatizes the product without the need for external oxidant. The Bu3Sn moiety, which is installed during the reaction sequence, allows further functionalization of the product via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of enynes into extended polycyclic structures of tunable dimensions.
Identifier: FSU_uspto_9708351 (IID), 9708351 (patent number), 2368265 (inventor key), 15/143669 (app id), 6c9256d97d167832cbab694dc904bd27 (assignee id)
Persistent Link to This Record: http://purl.flvc.org/fsu/fd/FSU_uspto_9708351
Use and Reproduction: Copyright not evaluated
Host Institution: FSU

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Alkenes as alkyne equivalents in radical cascades terminated by fragmentations. (2017). Alkenes as alkyne equivalents in radical cascades terminated by fragmentations. Retrieved from http://purl.flvc.org/fsu/fd/FSU_uspto_9708351