Two Stereoinduction Events in One C−H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes |
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| Authors: | Quentin Dherbassy Jean‐Pierre Djukic Joanna Wencel‐Delord Françoise Colobert |
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| Affiliation: | 1. Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg/Université de haute Alsace, ECPM, Strasbourg, France;2. Institut de Chimie de Strasbourg (UMR 7177), Université de Strasbourg, Strasbourg Cedex, France |
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| Abstract: | Herein we disclose the synthesis of original chiral scaffolds—ortho‐orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C?H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo‐stereoselective C?H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho‐terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N‐Biax and diphosphine BiaxPhos. |
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| Keywords: | asymmetric C− H activation atropisomerism axial chirality chiral ligands sulfoxides |
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