Journal
TETRAHEDRON
Volume 71, Issue 26-27, Pages 4445-4449Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.04.019
Keywords
Transmetalation; Boron; Oxygen; Gold; Alkoxyboration
Categories
Funding
- National Institutes of Health [1R01GM098512-01]
- Alexander von Humboldt Foundation
- UC-Regents
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Electronic effects in the transmetalation of an aryl group from gold to boron were investigated by NMR spectroscopy. The transmetalation reaction is more facile for increasingly electrophilic boron reagents and is in equilibrium under certain conditions. Observed tetracoordinate boronate compounds suggest a two-step, associative transmetalation reaction mechanism in which the organogold complex first delivers a nucleophilic phenyl group to the empty p orbital of boron. For certain substrates, this tetracoordinate intermediate decomposes to the tricordinate, final transmetallation product, and in others this tricordinate species remains in equilibrium with a tetracoordinate anionic boron compound. Experimental and theoretical investigations into the extension of this transmetalation reaction from a mechanistic step in our previously reported intramolecular gold-catalyzed addition of boron oxygen a bonds across alkynes to an intermolecular variant are discussed. (C) 2015 Published by Elsevier Ltd.
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