Stille coupling with C-N bond cleavage

October 1, 2016

Amine and aniline groups occur widely in natural products, pharmaceuticals and functional materials. A joint research group from the University of Tokyo, RIKEN CSRS and Tokushima Bunri University has developed a new method for direct conversion of C–N bonds, which are considered chemically inert.

Currently, many synthetic methods through C–H bond functionalization of petroleum-based materials have been established, leading to various types of practically useful compounds. On the other hand, new methods that allow direct conversion of natural resources and functional molecules are urgently needed for meeting the future environmental/energy demands. Since many natural products and functional molecules are highly oxidized, innovative methods that enable functionalization of C–O/C–N bonds provide efficient ways for utilization of such resources. However, C–O and C–N bonds are generally stable and difficult to be transformed in many chemical reactions. In a world first, this joint research group has pioneered a Stille coupling reaction via C–N bond cleavage. The method holds promise as a new route for creating functional molecules such as p-conjugated materials, pharmaceuticals, and bioactive compounds.


Original article
Nature Communications doi:10.1038/NCOMMS12937
D-Y. Wang, M. Kawahata, Z-K. Yang, K. Miyamoto, S. Komagawa, K. Yamaguchi, C. Wang, M. Uchiyama,
"Stille Coupling via C–N Bond Cleavage".

Masanobu Uchiyama
Team Leader
Advanced Elements Chemistry Research Team