Hydroboration with Pyridine Borane at Room Temperature

Julia M. Clay and Edwin Vedejs*
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109
J. Am. Chem. Soc., 2005, 127 (16), pp 5766–5767
DOI: 10.1021/ja043743j
Publication Date (Web): March 29, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, edved@umich.edu

Abstract

Abstract Image

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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History

  • Published In Issue April 27, 2005
  • Received October 14, 2004

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