Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 15, Pages 5946-5953Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406096
Keywords
atom transfer; cross-coupling; Grignard reaction; iron; radical reactions
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Funding
- Swedish Research Council
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The radical nature of iron-catalyzed cross-coupling between Grignard reagents and alkyl halides has been studied by using a combination of competitive kinetic experiments and DFT calculations. In contrast to the corresponding coupling with aryl halides, which commences through a classical two-electron oxidative addition/reductive elimination sequence, the presented data suggest that alkyl halides react through an atom-transfer-initiated radical pathway. Furthermore, a general iodine-based quenching methodology was developed to enable the determination of highly accurate concentrations of Grignard reagents, a capability that facilitates and increases the information output of kinetic investigations based on these substrates.
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