Directed C-H activation has been a topic of much interest due to its ability to increase substrate scope and reduce synthetic steps. Substantial progress has been made by placing directing groups on the substrate. One limitation of this approach is that it involves the addition and subsequent removal of these directing groups which can lower yields and lengthen the synthetic route. One possible approach involves using a ligand to regioselectively direct C-H activation. We are investigating ligands that coordinate to heteroatoms for directed C-H activation. In an attempt to contribute a new method for heterofunctionalization of alkenes, we discovered that in presence of catalytic amount of copper (II) triflate, a mixture of cinnamyl alcohol and phenyl boronic acid cyclize to form a diphenyl product. The product was then readily hydrolyzed to give the 1, 3 diol. Optimization of the reaction produced high yields. A variety of cinnamyl and allylic alcohol derivatives were used to show the scope of the reaction. Further studies using chiral boronic acids will be investigated to determine the enantioselective extent of the reaction.

New ligand design for C (SP3) H activation and boron-templated, acid-catalyzed cyclization of allylic alcohols to form 1, 3 diols

2019 Spring National Meeting

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