Mechanistic Studies of Catalytic Carbon–Carbon Cross-Coupling by Well-Defined Iron NHC Complexes

Jacob A. Przyojski (1519564)
Kevin P. Veggeberg (1519561)
Hadi D. Arman (1348743)
Zachary J. Tonzetich (1502530)

Publication date

October 2015

DOI

10.1021/acscatal.5b01445.s001

Abstract

The mechanism of iron-catalyzed carbon–carbon cross-coupling reactions between Grignard reagents and alkyl halides has been investigated using well-defined N-heterocyclic carbene (NHC) compounds. The iron(II) precatalyst, [Fe2Cl2(μ-Cl)2(IPr)2], was employed in several C–C cross coupling reactions exhibiting the ability to efficiently couple primary and secondary alkyl halides with several aryl and alkyl Grignard reagents. For selected substrates, a 2 mol % catalyst loading (4 mol % Fe) afforded conversions of >99% and were achieved with <8% homocoupling of the electrophile. The mechanism of the coupling reaction was studied by means of radical clock, radical trap, and single-turnover experiments,...

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Mechanistic Studies of Catalytic Carbon–Carbon Cross-Coupling by Well-Defined Iron NHC Complexes

Abstract

Extracted data

Mechanistic Studies of Catalytic Carbon–Carbon Cross-Coupling by Well-Defined Iron NHC Complexes

Abstract

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