Abstract
The mechanism of a recently reported Suzuki coupling reaction of quinoline-derived allylic N,O-acetals has been studied using a combination of structural, stereochemical, and kinetic isotope effect experiments. The data indicate that C-O activation is facilitated by Lewis acid assistance from the boronic acid coupling partner and an ionic SN1-like mechanism accounts for oxidative addition. In this context, we demonstrate the first direct observation of oxidative addition to a quinolinium salt. Notably, this mechanism is distinct from the more commonly described SN2(')-type oxidative addition of low-valent transition metals to most allylic electrophiles.
Original language | English (US) |
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Pages (from-to) | 16967-16970 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 134 |
Issue number | 41 |
DOIs | |
State | Published - Oct 17 2012 |
All Science Journal Classification (ASJC) codes
- General Chemistry
- Biochemistry
- Catalysis
- Colloid and Surface Chemistry