C-C bond formationO 0282 DOI: 10.1002/chin.201213051

Copper-Free Sonogashira Cross-Coupling for Functionalization of Alkyne-En-coded Proteins in Aqueous Medium and in Bacterial Cells. — A new and robust aminopyrimidine—palladium(II) complex is used for copper-free Sonogashira cross-coupling of various aryl iodides with terminal alkyne-containing peptide and pro-tein substrates in aqueous medium. A wide range of aromatic groups including fluoro-phores and fluorinated aromatic compounds can be readily introduced into the homo-propargylglycine (HPG)-containing ubiquitin under mild conditions with good yields. The suitability of this new method for functionalization of HPG-encoded ubiquitin in Escherichia coli is also demonstrated. — (LI, N.; LIM, R. K. V.; EDWARDRAJA, S.; LIN*, Q.; J. Am. Chem. Soc. 133 (2011) 39, 15316-15319, http://dx.doi.org/10.1021/ja2066913 ; Dep. Chem., State Univ. N. Y., Buffalo, NY 14260, USA; Eng.) — S. Adam

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