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Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes.


ABSTRACT: Radical α-C-H functionalization of alk-5-enyl boronic esters with concomitant functionalization of the alkene moiety is reported. These cascades comprise perfluoroalkyl radical addition to the alkene moiety of a boronate complex, intramolecular hydrogen atom transfer (HAT), single electron oxidation, and 1,2-alkyl/aryl migration. The boronate complexes are readily generated in situ by reaction of the alkenyl boronic esters with alkyl or aryl lithium reagents. Products are formed in a divergent approach by varying carbon radical precursors as well as alkyl/aryl lithium donors, and reactions proceed under mild conditions upon UV irradiation.

SUBMITTER: Wang D 

PROVIDER: S-EPMC8353630 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes.

Wang Dinghai D   Jana Kalipada K   Studer Armido A  

Organic letters 20210714 15


Radical α-C-H functionalization of alk-5-enyl boronic esters with concomitant functionalization of the alkene moiety is reported. These cascades comprise perfluoroalkyl radical addition to the alkene moiety of a boronate complex, intramolecular hydrogen atom transfer (HAT), single electron oxidation, and 1,2-alkyl/aryl migration. The boronate complexes are readily generated in situ by reaction of the alkenyl boronic esters with alkyl or aryl lithium reagents. Products are formed in a divergent a  ...[more]

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