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An Efficient Route to Isochromene Derivatives via Cascade Radical Cyclization and Radical‐Radical Coupling
Author(s) -
Yu Kaili,
Li Minyan,
Deng Guogang,
Liu Chunxiang,
Wang Jing,
Liu Zhengfen,
Zhang Hongbin,
Yang Xiaodong,
Walsh Patrick J.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900497
Subject(s) - chemistry , radical cyclization , propargyl , allylic rearrangement , radical , pharmacophore , aryl , ether , radical initiator , aryl radical , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry , stereochemistry , alkyl , monomer , polymer
Isochromenes are important pharmacophores present in biologically active molecules and natural products. Their synthesis is generally limited to cyclization of phenyl propargyl ether precursors under transition metal catalyzed conditions. Herein, we present a novel disconnection that rapidly constructs isochromene derivatives through a cascade radical cyclization strategy. Generation of aryl radicals by SET reduction of 2‐iodo benzyl allenyl ethers is followed by radical cyclization to construct the isochromene core with formation of an allylic radical. The allylic radical then undergoes coupling with the azaallyl radical to give products in good to excellent yields. The elaborated 2‐iodo phenyl propargyl ether precursors can be used to construct isochromenes bearing various functional groups.