3 years ago

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

Carboxylate-Assisted Formation of Aryl-Co(III) Masked-Carbenes in Cobalt-Catalyzed C–H Functionalization with Diazo Esters
Xavi Ribas, Anna Company, Teodor Parella, Vlad Martin-Diaconescu, Steven Roldán-Gómez, Josep M. Luis, Oriol Planas
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07880

DOI: 10.1021/jacs.7b07880

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