Photoinduced Synthesis of Dibenzofurans. Intramolecular and Intermolecular Comparative Methodologies.

PIERINI, ADRIANA BEATRIZ; CAMARGO SOLÓRZANO, PATRICIA; JIMENEZ, LILIANA BEATRIZ; BRIGANTE, FEDERICO

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Año: 2018 vol. 83 p. 7867 - 7877

0022-3263

The SRN1 reaction has been used as a powerful tool for the synthesis of heterocycles, only few studies about photoinduced intramolecular cyclization to generate a new C-O bond by a radical pathway have been reported. This work introduces two strategies for the synthesis of substituted dibenzofurans by electron transfer (eT) reactions. The first one is a three-step process that comprises bromination of o-arylphenols, Suzuki-Miyaura cross-coupling and photoinduced cyclization in order to obtain the above-mentioned products. The second one is a metal-free procedure and does not require any photocatalyst. Different solvents were tested and the yields ranged from low to moderate. A comparison was established between both methodologies showing the second one is the most suitable for the synthesis of dibenzofurans.