Lancaster borane, C6F5BH2xSMe2, was synthesized and reacted with BINOL in various solvents. In THF, the chiral monomeric boronic ester C6F5B(binolate) was isolated as its THF adduct, while in diethyl ether the bis-boronic ester (C6F5B)2(binolate)2was formed and characterized by NMR spectroscopy and X-ray analysis. The relative Lewis acid strength was estimated via the classical Gutmann method. The structural, Lewis acid-base and catalytic chemistry of these chiral BINOL based boronic esters will be discussed in detail.

C6F5B-Binolate: Synthesis, structure, Lewis acid–base chemistry and catalytic activity

2019 Fall National Meeting

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