Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of alpha,beta-Unsaturated Compounds and Alkynes

Autor(es)

de Souza, Gabriela F. P. ; Salles, Airton G.

• Tipo de documento: Artigo Científico
• Fonte: JOVE-JOURNAL OF VISUALIZED EXPERIMENTS; v. N/A, n. 154, p. 6-pg., 2019-12-01.

Resumo

Benzannulation reactions represent an effective protocol to transform acyclic building blocks into structurally varied benzene skeletons. Despite classical and recent approaches toward functionalized benzenes, in water metal-free methods remains a challenge and represents an opportunity to expand even more the set of tools used to synthesize polysubstituted benzene compounds. This protocol describes an operationally simple experimental setup to explore the benzannulation of alpha,beta-unsaturated compounds and alkynes to afford unprecedented functionalized benzene rings in high yields. Ammonium persulfate is the reagent of choice and brings notable advantages as stability and easy handling. Moreover, the use of water as a solvent and the absence of metals impart more sustainability to the method. A modified workup procedure that avoids the use of drying agents also adds convenience to the protocol. The purification of the products is performed using only a plug of silica. The substrate scope is currently limited to terminal alkynes and alpha,beta-unsaturated aliphatic compounds. (AU)

• Processo FAPESP: 17/18400-6 - Oxidação alílica/benzílica seguida de adição de Michael/reação aldólica em um único frasco: Uso do TBAI como catalisador comum para ambas as etapas visando aumento da complexidade estrutural.
• Beneficiário: Airton Goncalves Salles Junior
• Modalidade de apoio: Auxílio à Pesquisa - Regular