Collect. Czech. Chem. Commun. 2009, 74, 1023-1034
Published online 2009-06-26 18:24:49

Bio- and air-tolerant carbon–carbon bond formations via organometallic ruthenium catalysis

Louis Adriaenssens, Lukáš Severa, Jan Vávra, Tereza Šálová, Jakub Hývl, Martina Čížková, Radek Pohl, David Šaman and Filip Teplý*

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


Selected [2+2+2] cycloadditions, alkene–alkyne coupling and fusion of enyne with diazo compound, all triggered by an artificial organometallic ruthenium catalyst are demonstrated to proceed under ambient aerobic aqueous conditions in presence of bodily fluids or cell lysate. To the best of our knowledge, these are the first examples of bio- and air-tolerant C–C bond formation catalyzed by an artificial organometallic compound.

Keywords: Ruthenium; Organometallic catalysis; C–C coupling; [2+2+2] Cycloadditions; Alkene–alkyne coupling; Enyne-diazocompound fusion; Alkynes; Arenes; Heterocycles; Nitrogen-based organic cations; N-heteroaromatic cations; Helical structures; Helquat; Bio-, air-, and water-tolerant transformations; E. coli cell lysate; Human serum; Bioorthogonal reactions; Non-coded biocompatible chemistry.

References: 63 live references.