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. 2005 Apr 27;127(16):5766-7.
doi: 10.1021/ja043743j.

Hydroboration with pyridine borane at room temperature

Julia M Clay  1 , Edwin Vedejs
Affiliations

Hydroboration with pyridine borane at room temperature

Julia M Clay et al. J Am Chem Soc. .

Erratum in

  • J Am Chem Soc. 2008 Aug 13;130(32):10828

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.

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