Work

NHC and nucleophile chelation effects on reactive iron( ii ) species in alkyl–alkyl cross-coupling

Year: 2018

Type: article

Abstract: ) to generate cross-coupled product with overall selectivity analogous to catalysis. The high resistance of this catalytic system to β-hydride elimination of the alkyl nucleophile is attributed to its chelation to iron through ligation of carbon and one oxygen of the acetal moiety of the nucleophile. In fact, alternative NHC ligands such as SIPr are less effective in catalysis due to their increased steric bulk inhibiting the ability of the alkyl ligands to chelate. Overall, this study identifies a novel alkyl chelation method to achieve effective alkyl-alkyl cross-coupling with iron(ii)-NHCs, provides direct structural insight into NHC effects on catalytic performance and extends the importance of iron(ii) reactive species in iron-catalysed cross-coupling.

Source: Chemical Science

DOI: 10.1039/c7sc04750a

Authors: Valerie E. Fleischauer, Salvador B. Muñoz III, Peter G. N. Neate, William W. Brennessel, Michael L. Neidig

Institution: University of Rochester

Language: English

Topic: N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: G1839915149, G3066615795, G9000037150, G9000175768