Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes
Name
nihms936565.pdf
Description
Accepted version
Size
754.92 KB
Format
Adobe PDF
Checksum (MD5)
d22886a548bc8ec2234d19f58784540f
Author(s)
Liu, Richard
Bae, Minwoo
Buchwald, Stephen Leffler
Date Issued
January 29, 2018
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Liu, Richard Y., Bae, Minwoo, and Buchwald, Stephen L. "Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes." Journal of the American Chemical Society 140, 5 (January 2018): 1627–1631 © 2018 American Chemical Society.
Version
Author's final manuscript
Abstract
Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading. Keywords: Amides; Ligands; Nitrogen compounds; Dehydration; Chemical reactions
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/jacs.8b00643
