Get access
Advertisement

Efficient Reduction of Esters to Aldehydes through Iridium-Catalyzed Hydrosilylation

Authors

  • Chen Cheng,

    1. Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)
    Search for more papers by this author
  • Prof. Dr. Maurice Brookhart

    Corresponding author
    1. Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)
    • Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)
    Search for more papers by this author

  • We gratefully acknowledge the financial support of the NSF as part of the Center for Enabling New Technologies through Catalysis (CENTC, Grant No. CHE-0650456). We thank Thomas Lyons for useful comments. A provisional patent on this work has been submitted.

Abstract

original image

Trumping DIBALH: A new method for reduction of esters to aldehydes through silyl acetal intermediates involves a single-step hydrosilylation catalyzed by a readily available iridium complex, [{Ir(coe)2Cl}2] (see scheme; coe=cyclooctene). The low catalyst loading, mild reaction conditions, high conversions, and broad substrate scope make this method a superior alternative to ester reduction using DIBALH.

Get access to the full text of this article

Ancillary