Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin

In this work, a regioselective synthesis of isocoumarins from 2-alkynylbenzoic acid is reported. The transformations proceed smoothly with good yields in water via a metal-free radical pathway. When catalytic TBAB is employed, the reaction provides various isocoumarin derivatives according to the st...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2019-07, Vol.75 (28), p.3850-3855
Main Authors: Wang, Yan-Hua, Qiu, Guanyinsheng, Zhou, Hongwei, Xie, Wenlin, Liu, Jin-Biao
Format: Article
Language:English
Subjects:
2-Alkynylbenzoic acid
Isobenzofuran
Isocoumarin
Metal-free
Radical cyclization
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In this work, a regioselective synthesis of isocoumarins from 2-alkynylbenzoic acid is reported. The transformations proceed smoothly with good yields in water via a metal-free radical pathway. When catalytic TBAB is employed, the reaction provides various isocoumarin derivatives according to the structures of the corresponding precursors. It is believed that TBAB serves as a phase transfer catalyst and radical initiator in the reaction. Compared to previous methodologies, the synthetic procedure reported herein provides a more environmentally benign route for the synthesis of isocoumarins. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.06.012