Planar Chiral Organoborane Lewis Acids Derived from Naphthylferrocene |
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| Authors: | Jiawei Chen Krishnan Venkatasubbaiah Dr. Thilagar Pakkirisamy Dr. Ami Doshi Dr. Andrej Yusupov Yesha Patel Roger A. Lalancette Prof. Dr. Frieder Jäkle Prof. Dr. |
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| Affiliation: | 1. Department of Chemistry, Rutgers University‐Newark, 73 Warren Street, Newark, NJ 07102 (USA), Fax: (+1)?973‐353‐1264;2. Current address: Inorganic and Physical Chemistry Department, Indian Institute of Science, Bangalore, 560 012 (India) |
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| Abstract: | Enantiomerically pure metalated 2‐(1‐naphthyl)ferrocene (NpFc) derivatives NpFcM (M=SnMe3, HgCl) were prepared and characterized by multinuclear NMR and UV/Vis spectroscopy, cyclic voltammetry, and elemental analysis. Optical rotation measurements were performed and the absolute configuration of the new planar chiral ferrocene species was confirmed by single‐crystal X‐ray diffraction analysis. The mercuriated species NpFcHgCl proved suitable as a reagent for the preparation of the chiral organoborane Lewis acid NpFcBCl2, which can in turn be converted to other ferrocenylboranes by replacement of Cl with nucleophiles. The highly Lewis acidic perfluoroarylborane derivatives NpFcB(C6F5)Cl and NpFcB(C6F5)2 were successfully prepared by treatment with CuC6F5. The structures were studied by single‐crystal X‐ray diffraction and variable‐temperature 19F NMR spectroscopy, which suggested that π stacking of a C6F5 group on boron with the adjacent naphthyl group is energetically favorable. UV/Vis absorption spectroscopy and cyclic voltammetry measurements were performed to examine the electronic properties of these novel redox‐active chiral Lewis acids. |
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| Keywords: | boron chirality ferrocenes ferrocenylboranes Lewis acids |
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