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Bidentate Boron Lewis Acids: Selectivity in Host–Guest Complex Formation
Authors:Philipp Niermeier  Sebastian Blomeyer  Younes K. J. Bejaoui  J. Louis Beckmann  Beate Neumann  Hans‐Georg Stammler  Norbert W. Mitzel
Abstract:Bidentate boron Lewis acids based on 1,8‐diethynylanthracene were synthesised in two steps by initial stannylation of the terminal alkynes and subsequent tin–boron exchange with different chloroboranes. The reactions were very selective, and the target compounds were obtained in high purity and good to excellent yields. Complexation experiments of 1,8‐bis[(diphenylboranyl)ethynyl]anthracene with nitrogen bases (pyridine, pyrimidine, TMEDA) afforded three stable adducts, which were structurally characterised by X‐ray diffraction. Competition experiments demonstrated the selective exchange of guests, and quantum‐chemical calculations provided information on their energetics. NMR experiments at low temperature gave insight into the dynamic behaviour of the TMEDA adduct.
Keywords:1,8-diethynylanthracene  host–  guest complexes  molecular recognition  poly-Lewis acids  tin–  boron exchange
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