A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

• Thines Kanagasundaram,
• Antje Timmermann,
• Carsten S. Kramer and
• Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

• Cancer Consortium (DKTK), Heidelberg, Germany 10.3762/bjoc.15.250 Abstract Background: Silicon rhodamines are of particular interest because of their advantageous dye properties (fluorescence- and biostability, quantum efficiency, tolerance to photobleaching). Therefore, silicon rhodamines find frequent

• gave access to silicon rhodamines in poor to moderate yields, we wanted to improve these first valuable experimental results. Results: The preparation of the xanthene triflate was enhanced and several boron sources were screened to find the optimal coupling partner. After optimization of the palladium

• catalyst, different substituted boroxines were assessed to explore the scope of the Pd-catalyzed cross-coupling reaction. Conclusions: A number of silicon rhodamines were synthesized under the optimized conditions in up to 91% yield without the necessity of HPLC purification. Moreover, silicon rhodamines

Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement

• Jessica Matthias,
• Thines Kanagasundaram,
• Klaus Kopka and
• Carsten S. Kramer

Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226

• .15.226 Abstract Background: Since their first synthesis, silicon xanthenes and the subsequently developed silicon rhodamines (SiR) gained a lot of attention as attractive fluorescence dyes offering a broad field of application. We aimed for the synthesis of a fluorinable pyridinyl silicon rhodamine for

• ; mitochondrial probe; near-infrared (NIR) dyes; one-pot reaction; silicon rhodamines; Introduction Since their first synthesis by Fu and co-workers in 2008 [1], silicon xanthenes and the subsequently developed silicon rhodamines (SiR) have drawn a lot of attention as attractive fluorescence dyes offering a

• photophysical properties of numerous silicon rhodamines leading to further insights into the correlation of the dyes’ chemical structure with their fluorogenic behavior [27]. Regarding the quantum yield, Hanaoka et al. have shown that introduction of methyl, methoxy or dimethylamine groups into the benzene