Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes

Dean, William Michael and Mindaugas, Šiaučiulis and Storr, Thomas E. and Lewis, William and Stockman, Robert A. (2016) Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes. Angewandte Chemie International Edition, 55 (34). pp. 10013-10016. ISSN 1521-3773

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Abstract

The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98% yield and greater than 99.5% enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution patterns and provides access to diverse areas of chemical space in three operationally simple steps from commercially available reagents. This strategy provides orthogonal access to electron-deficient heteroaromatic compounds, traditionally synthesised via transition metal-catalysed cross-couplings, which circumvents common issues associated with proto-demetalation and β-hydride elimination.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: W. M. Dean, M. Šiaučiulis, T. E. Storr, W. Lewis, R. A. Stockman, Angew. Chem. Int. Ed. 2016, 55, 10013, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201602264/full. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Keywords: sp2-sp3 coupling, Sulfoxide, Ligand coupling, Diarylmethane, Sulfurane
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/anie.201602264
Depositing User: Smith, Ruth
Date Deposited: 12 May 2017 07:35
Last Modified: 25 Jul 2017 16:48
URI: http://eprints.nottingham.ac.uk/id/eprint/42752

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