Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 40, Pages 13285-13293Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8045519
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Funding
- NIH NIGMS [RO1 GM073836]
- Arnold and Mabel Beckman Foundation
- Abbott
- Amgen
- AstraZeneca
- Boehringer-Ingelheim
- Bristol Myers Squibb
- Eli Lilly
- GlaxoSmithKline
- Merck Research Laboratories
- Roche
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This paper describes a detailed investigation of factors controlling the dominance of a directing group in Pd-catalyzed ligand-directed arene acetoxylation. Mechanistic studies, involving reaction kinetics, Hammett analysis, kinetic isotope effect experiments, and the kinetic order in oxidant, have been conducted for a series of different substrates. Initial rates studies of substrates bearing different directing groups showed that these transformations are accelerated by the use of electron-withdrawing directing groups. However, in contrast, under conditions where two directing groups are in competition with one another in the same reaction flask, substrates with electron-donating directing groups react preferentially. These results are discussed in the context of the proposed mechanism for Pd-catalyzed arene acetoxylation.
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