Cobalt co-catalysis for cross-electrophile coupling: Diarylmethanes from benzyl mesylates and aryl halides

Laura K.G. Ackerman, Lukiana L. Anka-Lufford, Marina Naodovic, Daniel J. Weix

Research output: Contribution to journalArticlepeer-review

114 Scopus citations

Abstract

The nickel-catalyzed cross-coupling of aryl halides with alkyl radicals derived from alkyl halides has recently been extended to couplings with carbon radicals generated by a co-catalyst. In this study, a new co-catalyst, cobalt phthalocyanine (Co(Pc)), is introduced and demonstrated to be effective for coupling substrates not prone to homolysis. This is because Co(Pc) reacts with electrophiles by an SN2 mechanism instead of by the electron-transfer or halogen abstraction mechanisms previously explored. Studies demonstrating the orthogonal reactivity of (bpy)Ni and Co(Pc), applying this selectivity to the coupling of benzyl mesylates with aryl halides, and the adaptation of these conditions to the less reactive benzyl phosphate ester and an enantioconvergent reaction are presented.

Original languageEnglish (US)
Pages (from-to)1115-1119
Number of pages5
JournalChemical Science
Volume6
Issue number2
DOIs
StatePublished - Feb 1 2015
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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