Hydrogen Atom Transfer (HAT)-Mediated Remote Desaturation Enabled by Fe/Cr-H Cooperative Catalysis
Year: 2023
Type: preprint
Abstract: A highly selective, remote desaturation reaction, catalyzed by an iron/chromium cooperative system, generates unsaturated amides from abundant starting materials. The reaction appears to operate via a triple hydrogen atom transfer (HAT) cascade: (i) A 1,5-HAT from a remote C–H bond to an iron nitrenoid; (ii) a chromium-hydride-mediated HAT to N-center, (iii) the abstraction of a second H• from the remote organic radical by the chromium radical Cr•. Unsaturated amides and conjugated dienamides can be prepared with good regio- and stereoselectivity. The synthetic utility of this method is verified by late-stage desaturation of natural product derivatives and biologically important molecules. Cooperation between the metals controls the sites of hydrogen atom transfer.
Source: Research Square
Authors: Jack Norton, Yanjun wan, Augustine Adda, Jin Qian, David Vaccaro, Peixian He, Gang Li
Institutions: Columbia University, Utah State University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4387245144