Development of a 9-borabicyclo[3.3.1]nonane-mediated solid-phase Suzuki coupling for the preparation of dihydrostilbene analogs
2003; Elsevier BV; Volume: 44; Issue: 14 Linguagem: Inglês
10.1016/s0040-4039(03)00415-5
ISSN1873-3581
AutoresRon D Ferguson, Ning Su, Roger A. Smith,
Tópico(s)Advanced Synthetic Organic Chemistry
ResumoA 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.
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