Synthesis of 1,4-Diketones with Low-Valent Titanium Species

• In Event: Poster Presentation and Judging for: Biomedical; Cell & Molecular Biology; Chemistry & Biochemistry; Marine Science; Systematics & Evolutionary Biology.
  In Poster Session: Chemistry & Biochemistry Poster Session

Abstract

A novel method for the formation of 1,4-diketones was developed using low-valent titanium species. The products of this novel methodology are industrially important precursors for the synthesis of bioactive compounds such as furans, pyrroles, and thiophenes. These heterocycles are commonly found in larger macrocycles such as heme, chlorins, chlorophyll, agrochemicals, and pharmaceuticals that function as biological inhibitors and DNA/RNA selective targeting reagents. The use of α-bromoketones affords 1,4-diketone synthesis in up to 81% yield and the scope of this reaction has been expanded to a variety of bromoacetophenone derivatives. This work represents a unique and under-explored reactivity manifold for homogeneous low-valent titanium compounds and represents the first implementation of this novel intermediate to the synthesis of complex molecules.

Author

• Nathan Le, Southwestern University