Inorganic bismuth(III) compounds can be used as low-cost and nontoxic Lewis acids. Organobismuth compounds have also been applied as reagents or catalysts in organic synthesis. However, these compounds are often air- and moisture-sensitive, which limits their practical use.
Renhua Qiu, Xinhua Xu, Shuang-Feng Yin, Hunan University, Changsha, China, and colleagues have developed an air- and water-stable Lewis-acidic organobismuth(V) compound, Ph3Bi(OSO2C8F17)2 (triphenyl bismuth(V) bisperfluorooctanesulfonate). The team synthesized the compound in quantitative yield by treating Ph3BiCl2 with C8F17SO2OAg in dichloromethane.
The researchers tested the compound’s catalytic activity and found high efficiency for the synthesis of nitrogen
heterocycles such as diindolylmethane derivatives, dihydropyrimidinones (pictured), dihydropyridines, and 1,2-disubstitued benzimidazoles. Additionally, the catalyst was stable and reusable. The team hopes it will find a broad range of applications in organic synthesis.
- Air-stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N-Containing Compounds,
Penghui Wang, Jinying Wang, Chak-Tong Au, Renhua Qiu, Xinhua Xu, Shuang-Feng Yina,
Adv. Synth. Catal. 2016.