AI Article Synopsis
- A series of 1,3- and 1,4-diboryl-1,3-cyclohexadienes were created using CoCp-mediated cocyclizations of alkynylboronic esters with alkenes, followed by iron(III) chloride-induced demetallation.
- The influence of substituents on the alkyne was examined, revealing that careful selection led to highly selective production of 1,3-diborylated cyclohexadienes, while 1,4-diborylated variants were sourced from diborylated diynes.
- The study explored the reaction's versatility, accommodating various types of alkenes, and utilized DFT computations to analyze the reaction mechanism and
Article Abstract
A series of 1,3- and 1,4-diboryl-1,3-cyclohexadienes have been prepared by intermolecular CoCp-mediated [2+2+2] cocyclizations of alkynylboronic pinacolate esters with alkenes, followed by oxidative demetallation with iron(III) chloride. The effect of substitution at the borylated alkyne on chemo- and regioselectivities has been studied, suggesting steric control. The proper choice of substituents allowed the preparation of 1,3-diborylated cyclohexadienes in a highly selective manner. Alternatively, 1,4-diborylated cyclohexadienes could be prepared from diborylated diynes. The scope of this reaction has been examined and found to include electron-poor, electron-rich, linear, and cyclic alkenes. The diborylated cyclohexadienes were submitted to single or double Suzuki-Miyaura cross-coupling reactions with haloarenes to afford polyarylated systems. The mechanism of the title reaction, including the regioselectivity of the cycloaddition steps, has been analyzed by means of DFT computations.
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| http://dx.doi.org/10.1002/chem.200700337 | DOI Listing |
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