Journal
TETRAHEDRON
Volume 67, Issue 24, Pages 4391-4396Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.066
Keywords
Cross-coupling; Mechanism; Hammett relationship; Transmetalation; Organosilicon
Categories
Funding
- National Institutes of Health [GM-63167]
- Aldrich Chemical Company
- Amgen
- University of Illinois
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The electronic characteristics of coupling partners in the transmetalation step for the cross-coupling reaction of arylsilanolates have been investigated. The ability to interrogate the transmetalation event by in situ preparation of the arylpalladium(II) silanolate intermediate has enabled a Hammett analysis for both the aryl electrophile and arylsilanolate to be conducted. These studies reveal that electron-donating groups on the silicon nucleophile and electron-withdrawing groups on the electrophile accelerate the transmetalation process. (C) 2011 Elsevier Ltd. All rights reserved.
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