Iridium-catalyzed hydrocarboxylation of 1,1-dimethylallene: byproduct-free reverse prenylation of carboxylic acids

Organic Letters
In Su Kim, Michael J Krische

Abstract

Exposure of carboxylic acids 1a-12a to commercially available 1,1-dimethylallene in the presence of substoichiometric quantities of an iridium catalyst prepared in situ from [Ir(cod)Cl]2 and BIPHEP provides the corresponding 1,1-dimethylallyl (reverse prenyl) esters 1b-12b in 74-92% isolated yield. This protocol represents the first branch-regioselective allene hydrocarboxylation. Stoichiometric byproducts are not generated in this process and protecting groups are not required for alcohols, phenols, and indolic amines.

References

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Feb 10, 2007·The Journal of Organic Chemistry·Ming-Yu NgaiMichael J Krische

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Citations

Jul 28, 2016·Accounts of Chemical Research·Philipp Koschker, Bernhard Breit
Jan 12, 2017·Journal of the American Chemical Society·Faben A Cruz, Vy M Dong
Jan 28, 2017·Journal of the American Chemical Society·Xiao-Hui Yang, Vy M Dong
Oct 30, 2016·Chemistry : a European Journal·Alexander M Haydl, Bernhard Breit
Jun 9, 2015·Chemical Communications : Chem Comm·Kun XuBernhard Breit
Jul 29, 2015·Chemical Communications : Chem Comm·Midori Nagamoto, Takahiro Nishimura
Jun 13, 2017·Angewandte Chemie·Alexander M HaydlMichael J Krische
Sep 30, 2008·The Journal of Organic Chemistry·Xiao-Qing ZhuJin-Pei Cheng
Apr 24, 2021·Journal of the American Chemical Society·Patrick D ParkerVy M Dong
Feb 5, 2011·Journal of the American Chemical Society·Alexandre LumbrosoBernhard Breit
Jun 14, 2013·Journal of the American Chemical Society·Christo S Sevov, John F Hartwig
Nov 25, 2011·Journal of the American Chemical Society·Philipp KoschkerBernhard Breit
Nov 5, 2014·Journal of the American Chemical Society·Kun XuBernhard Breit
Aug 3, 2019·The Journal of Organic Chemistry·Rémi BlieckFlorian Monnier
Feb 11, 2015·Journal of the American Chemical Society·Philipp KoschkerBernhard Breit

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