Study of a new rate increasing "base effect" in the palladium-catalyzed amination of aryl iodides

The Journal of Organic Chemistry
Caroline MeyersRoger A Dommisse

Abstract

Evidence for an interphase deprotonation of Pd(II)-amine complexes with weak carbonate base has been gained for the first time. When a rate-limiting deprotonation step is involved in the catalytic cycle, controlling the structure (shape and size of the particles) and/or molar excess of the carbonate base used can significantly increase the reaction rate of Buchwald-Hartwig aminations. By taking such a "base effect" into account a general protocol for the intermolecular amination of aryl iodides with all types of amines has been developed based on a standard Pd-BINAP catalyst, using cesium carbonate as the base.

References

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Citations

Nov 17, 2007·Nature Protocols·Ryan A AltmanStephen L Buchwald
Dec 20, 2011·Chemistry : a European Journal·Ka Hou Hoi, Michael G Organ
Jan 29, 2008·Chemistry : a European Journal·Michael G OrganCory Valente
Sep 23, 2006·Organic & Biomolecular Chemistry·Irene C Christoforou, Panayiotis A Koutentis
Jan 1, 2011·Chemical Science·David S Surry, Stephen L Buchwald
Jan 10, 2012·Chemical Society Reviews·Tom R M Rauws, Bert U W Maes
Jun 6, 2019·Angewandte Chemie·Ruth DorelAlexander M Haydl
Jul 1, 2021·Chemistry : a European Journal·Volodymyr SemeniuchenkoMichael G Organ
Oct 29, 2014·Organic Letters·Benjamin A ChalmersKye-Simeon Masters
Mar 23, 2018·The Journal of Organic Chemistry·Hyunseok KimPhil Ho Lee
Jul 6, 2014·Organic Letters·Xiao Yun ChenCarsten Bolm
Mar 13, 2018·Journal of the American Chemical Society·Joseph M DennisStephen L Buchwald
Feb 11, 2020·Journal of the American Chemical Society·Richard Y LiuStephen L Buchwald
May 1, 2019·The Journal of Organic Chemistry·Zicong ChenChau Ming So
Feb 10, 2012·The Journal of Organic Chemistry·Jeffrey S CannonNicole S Solomon
Dec 7, 2019·The Journal of Organic Chemistry·Christopher JanotChristophe Aïssa
Nov 13, 2020·Journal of the American Chemical Society·Sii Hong LauBrad P Carrow

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