Strongly Directing Substituents in the Radical Arylation of Substituted Benzenes
Although general interest in radical arylation reactions has grown rapidly in recent years, poor regioselectivities and the need to use a large excess of the radical-accepting arene have hindered their application to substituted benzenes. We now describe experimental and computational investigations into the substituent effects that lead to regioselective addition based on the recent discovery of anilines as outstanding substrates for radical arylations.
Hofmann, Josefa,Clark, Timothy,Heinrich, Markus R.
p. 9785 - 9791
(2016/10/31)
Palladium-catalyzed direct arylation of phenols with aryl iodides
An efficient protocol of palladium-catalyzed direct para-arylation of unfunctionalized phenols with aryl iodides under mild conditions was reported. A variety of substrates were applied in this reaction with yields up to 87%.
Regioselective radical arylation of anilines with arylhydrazines
Substituted 2-aminobiphenyls have been prepared from arylhydrazines and anilines via radical arylation reactions under simple oxidative conditions. The strong directing effect of the free and unprotonated amino functionality leads to high regioselectivities, and anilines have been shown to be significantly better aryl radical acceptors than nitrobenzenes or phenyl ethers. The methodology is also applicable to phenols, which react best as phenolates under strongly basic conditions. Finally, radical arylation reactions of anilines and anilinium salts under various conditions have for the first time demonstrated that regioselectivity can also be controlled through the rearomatization step and that the addition of an aryl radical to a substituted benzene might even be reversible.
Jasch, Hannelore,Scheumann, Julia,Heinrich, Markus R.
p. 10699 - 10706
(2013/02/25)
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