Mechanistic investigation of iridium-catalyzed C-H borylation of methyl benzoate: Ligand effects in regioselectivity and activity

Jesús Jover, Feliu Maseras

Research output: Contribution to journalArticleResearchpeer-review

12 Citations (Scopus)

Abstract

© 2016 American Chemical Society. The Ir-catalyzed C-H borylation of methyl benzoate has been studied with DFT methodology in order to understand the experimentally observed ligand-induced regioselectivity and activity when different [(ligand)Ir(Bpin)3] catalysts are employed. While bidentate ligands such as 4,4′-di-tBu-2,2′-bipyridine (dtbpy) completely inhibit ortho-borylation, the use of selected triphenylphosphine derivatives enables the reaction on that position, avoiding the meta- and para-regioisomers. The analysis of the catalytic cycles for the borylation reactions with dtbpy, PPh3, P(p-CF3C6H4)3, and P(m,m-(CF3)2C6H3)3 allows the interpretation of the observed ligand effects. The different reactivity observed for the different monodentate phosphine ligands can also be rationalized in terms of catalyst stability.
Original languageEnglish
Pages (from-to)3221-3226
JournalOrganometallics
Volume35
Issue number18
DOIs
Publication statusPublished - 26 Sep 2016

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