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Synthesis of 3-(Bromomethylene)isobenzofuran-1(3H)-ones through regioselective 5-exo-dig bromocyclization of 2-alkynylbenzoic acids

Author:
Zheng, Yannan, Liu, Mengli, Qiu, Guanyinsheng, Xie, Wenlin, Wu, Jie
Source:
Tetrahedron 2019 v.75 no.12 pp. 1663-1668
ISSN:
0040-4020
Subject:
acids, chemical structure, cross-coupling reactions, organic compounds, regioselectivity
Abstract:
A direct synthesis of 3-(bromomethylene)isobenzofuran-1(3H)-ones from 2-alkynylbenzoic acids is developed through a regioselective 5-exo-dig bromocyclization. The reaction proceeds smoothly with a broad substrate scope. The products can be further elaborated via a palladium-catalyze cross-coupling reaction, or can convert to other heterocycles through simple operation. Preliminary mechanistic studies reveal that this transformation undergoes a radical process.
Agid:
6251133