Identification of a higher-order organozincate intermediate involved in Negishi cross-coupling reactions by mass spectrometry and NMR spectroscopy

Howard N Hunter; Niloufar Hadei; Voislav Blagojevic; Pascal Patschinski; George T Achonduh; Stephanie Avola; Diethard K Bohme; Michael G Organ

doi:10.1002/chem.201101029

Identification of a higher-order organozincate intermediate involved in Negishi cross-coupling reactions by mass spectrometry and NMR spectroscopy

Chemistry. 2011 Jul 4;17(28):7845-51. doi: 10.1002/chem.201101029. Epub 2011 Jun 8.

Authors

Howard N Hunter¹, Niloufar Hadei, Voislav Blagojevic, Pascal Patschinski, George T Achonduh, Stephanie Avola, Diethard K Bohme, Michael G Organ

Affiliation

¹ Department of Chemistry, York University, 4700 Keele St., Toronto, M3J 1P3, Canada.

PMID: 21656863
DOI: 10.1002/chem.201101029

Abstract

Negishi cross-coupling reactions were analyzed in solution by mass spectrometry and NMR spectroscopy to identify both the effect of LiBr as an additive as well as the purpose of 3-dimethyl-2-imidazolidinone (DMI) as a co-solvent. The results suggest that the main role of DMI is to facilitate a higher order bromozincate formation during the addition of LiBr.