Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes
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...
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| Format: | Article |
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Wiley-VCH Verlag
2016
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| Online Access: | https://eprints.nottingham.ac.uk/42752/ |
| _version_ | 1848796558890369024 |
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| author | Dean, William Michael Mindaugas, Šiaučiulis Storr, Thomas E. Lewis, William Stockman, Robert A. |
| author_facet | Dean, William Michael Mindaugas, Šiaučiulis Storr, Thomas E. Lewis, William Stockman, Robert A. |
| author_sort | Dean, William Michael |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:49:54Z |
| format | Article |
| id | nottingham-42752 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:49:54Z |
| publishDate | 2016 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-427522020-05-04T18:07:24Z https://eprints.nottingham.ac.uk/42752/ Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes Dean, William Michael Mindaugas, Šiaučiulis Storr, Thomas E. Lewis, William Stockman, Robert A. 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. Wiley-VCH Verlag 2016-08-09 Article PeerReviewed Dean, William Michael, Mindaugas, Šiaučiulis, Storr, Thomas E., 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 sp2-sp3 coupling Sulfoxide Ligand coupling Diarylmethane Sulfurane http://onlinelibrary.wiley.com/doi/10.1002/anie.201602264/full doi:10.1002/anie.201602264 doi:10.1002/anie.201602264 |
| spellingShingle | sp2-sp3 coupling Sulfoxide Ligand coupling Diarylmethane Sulfurane Dean, William Michael Mindaugas, Šiaučiulis Storr, Thomas E. Lewis, William Stockman, Robert A. Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes |
| title | Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes |
| title_full | Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes |
| title_fullStr | Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes |
| title_full_unstemmed | Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes |
| title_short | Versatile C(sp2)−C(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes |
| title_sort | versatile c(sp2)−c(sp3) ligand couplings of sulfoxides for the enantioselective synthesis of diarylalkanes |
| topic | sp2-sp3 coupling Sulfoxide Ligand coupling Diarylmethane Sulfurane |
| url | https://eprints.nottingham.ac.uk/42752/ https://eprints.nottingham.ac.uk/42752/ https://eprints.nottingham.ac.uk/42752/ |