Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen

Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen
Michele Mari, Giovanni Piersanti, Giovanni Di Gregorio, Francesca Bartoccini
We present the coupling of primary and secondary benzyl alcohols with indoles to form 3-benzylated indoles and H2O that is catalyzed, for the first time, by a complex of earth-abundant iron. This transformation accommodates a variety of substrates and is distinguished by its operational simplicity, sustainability, high functional-group tolerance, and amenability to gram-scale synthesis. On the basis of the preliminary experimental observations, we propose that the reaction proceeds through a borrowing hydrogen process.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01603

DOI: 10.1021/acs.joc.7b01603

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