Development of a 9-borabicyclo[3.3.1]nonane-mediated solid-phase Suzuki coupling for the preparation of dihydrostilbene analogs

A novel 9-borabicyclo[3.3.1]nonane-mediated solid-phase Suzuki coupling was developed to generate dihydrostilbenes (bibenzyls) and related compounds. Using optimized conditions (20 mol% PdCl2(dppf), 10 equiv. Et3N, and 10 equiv. olefin/9-BBN, in 9:1 DMF/H2O, 50°C, 18 h), high conversions to desired products were generally obtained. A small combinatorial library of derivatives was successfully prepared via radiofrequency tagging and directed sorting techniques.