Iridium- and Rhodium-Catalyzed Directed C-H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents

Organic Letters
Erwann Grenet, Jerome Waser

Abstract

The C-H heteroarylation of benzaldehydes with indoles and pyrroles was realized using the benziodoxolone hypervalent iodine reagents indole- and pyrroleBX. Functionalization of the aldehyde C-H bond using either an o-hydroxy or amino directing group and catalyzed by an iridium or a rhodium complex allowed the synthesis of salicyloylindoles and (2-sulfonamino)benzoylindoles, respectively, with good to excellent yields (74-98%). This new transformation could be carried out under mild conditions (rt to 40 °C) and tolerated a broad range of functionalities, such as ethers, halogens, carbonyls, or nitro groups.

References

Jan 1, 1995·Life Sciences·R PertweeA Makriyannis
Jul 20, 2006·Proceedings of the National Academy of Sciences of the United States of America·Amol M PatwardhanKenneth M Hargreaves
Feb 6, 2008·Accounts of Chemical Research·Young Jun ParkChul-Ho Jun
Jul 22, 2008·Bioorganic & Medicinal Chemistry Letters·Eugene L Piatnitski CheklerJacqueline F Doody
May 7, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·María A Garralda
Oct 31, 2009·Chemical Reviews·Michael C Willis
Apr 30, 2011·The Journal of Organic Chemistry·Sankar K GuchhaitHarshad Kamble
Jan 21, 2012·Chemical Communications : Chem Comm·Ying-Xiu LiYong-Min Liang
Sep 21, 2013·The Journal of Antibiotics·Philipp JetterGerhard Bringmann
Dec 3, 2014·European Journal of Medicinal Chemistry·Ming-Zhi ZhangGuang-Fu Yang
Jul 15, 2015·Bioorganic & Medicinal Chemistry·Hsueh-Yun LeeJing-Ping Liou
Feb 11, 2016·Chemical Reviews·Akira Yoshimura, Viktor V Zhdankin
Nov 24, 2016·Chemistry, an Asian Journal·Kazuma IshidaKatsuhiko Moriyama
Aug 11, 2017·Chemistry : a European Journal·Paola CaramentiJerome Waser
Nov 1, 2017·Chemistry, an Asian Journal·Bin WuNaohiko Yoshikai

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Citations

May 5, 2018·Chemistry : a European Journal·Paola CaramentiJerome Waser
Aug 3, 2019·Organic & Biomolecular Chemistry·I F Dempsey HyattCyrus Mowdawalla
Jun 9, 2020·Chemistry, an Asian Journal·Jinkui ChaiNaohiko Yoshikai

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