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Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2‐Azaallyls
Author(s) -
Deng Guogang,
Li Minyan,
Yu Kaili,
Liu Chunxiang,
Liu Zhengfen,
Duan Shengzu,
Chen Wen,
Yang Xiaodong,
Zhang Hongbin,
Walsh Patrick J.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812369
Subject(s) - benzofuran , chemistry , intermolecular force , radical cyclization , cascade , aryl , combinatorial chemistry , radical , stereochemistry , organic chemistry , molecule , alkyl , chromatography
Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Single‐electron transfer (SET) from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling. This expedient approach enables the synthesis of a range of polycyclic benzofurans that would otherwise be difficult to prepare.