Carboxylate-Assisted Formation of Aryl-Co(III) Masked-Carbenes in Cobalt-Catalyzed C-H Functionalization with Diazo Esters

Oriol Planas, Steven Roldán-Gómez, Vlad Martin-Diaconescu, Teodor Parella, Josep M. Luis, Anna Company, Xavi Ribas

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    17 Citations (Scopus)

    Abstract

    © 2017 American Chemical Society. Herein we describe the synthesis of a family of aryl-Co(III)-carboxylate complexes and their reactivity with ethyl diazoacetate. Crystallographic, full spectroscopic characterization, and theoretical evidence of unique C-metalated aryl-Co(III) enolate intermediates is provided, unraveling a carboxylate-assisted formation of aryl-Co(III) masked-carbenes. Moreover, additional evidence for an unprecedented Co(III)-mediated intramolecular SN2-type C-C bond formation in which the carboxylate moiety acts as a relay is disclosed. This novel strategy is key to tame the hot reactivity of a metastable Co(III)-carbene and elicit C-C coupling products in a productive manner.
    Original languageEnglish
    Pages (from-to)14649-14655
    JournalJournal of the American Chemical Society
    Volume139
    Issue number41
    DOIs
    Publication statusPublished - 18 Oct 2017

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