Solid-phase synthesis of iterative RAFT single unit monomer insertion adducts

In this article, we disclose the use of a solid-phase methodology to synthesise iterative RAFT single unit monomer insertion (SUMI) adducts. This methodology features a reversible thiocarbonylthio protecting group and radical chain growth of vinyl monomers, with minimal purification required during the synthesis. To achieve this, a RAFT chain transfer agent was immobilised on a common peptide synthesis resin via the R-group in the first instance. Using an oxygen-tolerant PET-RAFT methodology, we then extended the iterative synthesis of indene-maleimide SUMI adducts to 18 units with minimal dispersity, completely unprecedented in SUMI chemistry. Furthermore, as we demonstrate, this solid-phase methodology can be generalised to other maleimide derivatives and other solid-phase resins. In this article, we disclose the use of a solid-phase methodology to synthesise iterative RAFT single unit monomer insertion (SUMI) adducts.

Automated summary

This article introduces a solid-phase methodology for synthesizing iterative RAFT single unit monomer insertion (SUMI) adducts. The method features a reversible thiocarbonylthio protecting group and radical chain growth of vinyl monomers, requiring minimal purification during the synthesis. By immobilizing the RAFT chain transfer agent on a common peptide synthesis resin, and using an oxygen-tolerant PET-RAFT methodology, the iterative synthesis of indene-maleimide SUMI adducts was extended to 18 units with minimal dispersity, which is unprecedented in SUMI chemistry. Furthermore, the solid-phase methodology can be applied to other maleimide derivatives and other solid-phase resins.