Iridium- and Rhodium-Catalyzed Directed C–H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents
Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fedérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland
Org. Lett., 2018, 20 (5), pp 1473–1476
DOI: 10.1021/acs.orglett.8b00337
Publication Date (Web): February 21, 2018
Copyright © 2018 American Chemical Society
*E-mail: jerome.waser@epfl.ch.
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.
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.8b00337.
- Experimental procedures, analytical data, optimization tables, and NMR spectra for all compounds (PDF)
- NMR data (ZIP)
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