Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 1, Pages 18-21Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5093166
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Funding
- NIH [GM-087605]
- NSF [CHE1213230]
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The first selective coupling of a carbon nucleophile with methyl, ethyl, propyl, and butyl arenes in the absence of a directing group is described. Pd(OAc)(2) double C-H activation displays remarkable selectivity for the terminal methyl sites in alkyl arenes, rather than the more commonly observed arene sp(2) C-H activation. Mechanistic studies indicate the intermediacy of an azlactone dimer, obtained from oxidation with Pd(OAc)(2), and are consistent with a Pd-catalyzed C-H activation vs a radical process. The observed reactivity establishes that typical reaction solvents (e.g., toluene) can readily participate in C-H activation chemistry.
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