Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes

Dean, William Michael; Mindaugas, �iau?iulis; Storr, Thomas E.; Lewis, William; Stockman, Robert A.

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.

Citation

Dean, W. M., Mindaugas, Š., Storr, T. E., Lewis, W., & Stockman, R. A. (2016). Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes. Angewandte Chemie International Edition, 55(34), 10013-10016. https://doi.org/10.1002/anie.201602264

• Journal Article Type: Article
• Acceptance Date: Apr 29, 2016
• Online Publication Date: Jul 20, 2016
• Publication Date: Aug 16, 2016
• Deposit Date: May 12, 2017
• Publicly Available Date: May 12, 2017
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 55
• Issue: 34
• Pages: 10013-10016
• DOI: https://doi.org/10.1002/anie.201602264
• Keywords: sp2-sp3 coupling, Sulfoxide, Ligand coupling, Diarylmethane, Sulfurane
• Public URL: https://nottingham-repository.worktribe.com/output/806100
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201602264/full
• 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.
• Contract Date: May 12, 2017