In:
Organic Chemistry Frontiers, Royal Society of Chemistry (RSC), Vol. 9, No. 17 ( 2022), p. 4676-4684
Abstract:
A metal-free switchable synthesis of 1,4-bridged dihydroisoquinoline-3-ones and isoquinoline-1,3,4-triones through the oxidation of isoquinolinium salts is described. 1,4-Bridged dihydroisoquinolin-3-ones were constructed for the first time via the sequential oxidation/annulation of isoquinolinium salts with 4-hydroxycoumarins. Meanwhile, the iodine( iii )-oxidized intermediates of isoquinolinium salt could be converted to isoquinoline-1,3,4-triones in high yields by treatment with tert -butyl hydroperoxide. These site-selective transformations rely on an iodine( iii )-mediated dual radical addition/radical coupling strategy and prove that the combination of the bromide anion and phenyliodine( iii ) diacetate is a useful carrier of relatively stable bromine radicals and highly labile carboxyl radicals.
Type of Medium:
Online Resource
ISSN:
2052-4129
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2022
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