Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal.

The Journal of Organic Chemistry
Vardan Papoian, Thomas Minehan

Abstract

Treatment of aryl iodides with indium metal in the presence of lithium chloride leads to the formation of an organoindium reagent capable of participating in cross-coupling reactions under transition-metal catalysis. Combination with aryl halides in the presence of 5 mol % Cl2Pd(dppf) furnishes biaryl compounds in good yields; similarly, reaction with acyl halides or allylic acetates/carbonates in the presence of 5-10 mol % palladium catalyst leads to arylketones and allylic substitution products, respectively, in moderate yields. The reactions are tolerant of the presence of protic solvents, and approximately 85% of the indium metal employed can be recovered by reduction of the residual indium salts with zinc(0).

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Citations

Nov 1, 2012·Chemical Reviews·Zhi-Liang ShenTeck-Peng Loh
Nov 6, 2013·Chemical Reviews·David TillyPhilippe C Gros
Oct 8, 2011·The Journal of Organic Chemistry·Gary A Molander, Laura Iannazzo
May 4, 2011·Chemistry, an Asian Journal·Kooyeon LeePhil Ho Lee
Nov 9, 2016·Chemical Society Reviews·Kai ZhaoTeck-Peng Loh
Aug 1, 2018·Archiv der Pharmazie·Linda KinenaAigars Jirgensons
Dec 23, 2008·The Journal of Organic Chemistry·Louis S ChupakYves A Chantigny
Dec 15, 2010·The Journal of Organic Chemistry·Phil Ho LeeHyonseok Hwang
Jun 13, 2019·Journal of the American Chemical Society·Kristof JessSuzanne A Blum
Oct 1, 2014·The Journal of Organic Chemistry·William ErbJérôme Blanchet
Aug 16, 2011·The Journal of Organic Chemistry·Laksmikanta Adak, Naohiko Yoshikai
Mar 12, 2021·Organometallics·Kristof JessSuzanne A Blum

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