Diisobutylaluminum Hydride Reductions Revitalized: A Fast, Robust, and Selective Continuous Flow System for Aldehyde Synthesis

Author(s)
Webb, Damien; Jamison, Timothy F.
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Abstract
A continuous flow system for the multiparameter (flow rate, temperature, residence time, stoichiometry) optimization of the DIBALH reduction of esters to aldehydes is described. Incorporating an in-line quench (MeOH), these transformations are generally complete in fewer than 60 s. Mixing of the DIBALH and ester solutions was observed to be an exceptionally critical parameter for optimum results. This system thus provides general guidelines based on the structure of the ester for selective reduction of an ester without overreduction.
Date issued
2011-12
URI
http://hdl.handle.net/1721.1/76286
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Webb, Damien, and Timothy F. Jamison. “Diisobutylaluminum Hydride Reductions Revitalized: A Fast, Robust, and Selective Continuous Flow System for Aldehyde Synthesis.” Organic Letters 14.2 (2012): 568–571.
Version: Author's final manuscript
ISSN
1523-7060
1523-7052
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