Hydroboration with Pyridine Borane at Room Temperature
- 29 March 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (16) , 5766-5767
- https://doi.org/10.1021/ja043743j
Abstract
Treatment of pyridine borane (Py·BH3) with iodine, bromine, or strong acids affords activated Py·BH2X complexes that are capable of hydroborating alkenes at room temperature. Evidence is presented for an unusual hydroboration mechanism involving leaving group displacement. In contrast to THF·BH3, hydroboration with Py·BH2I selectively affords the monoadducts. The crude hydroboration products are converted into synthetically useful potassium alkyltrifluoroborate salts upon treatment with methanolic KHF2.Keywords
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