Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 20, Pages 7859-7867Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c03780
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Funding
- National Science Foundation Center for Synthetic Organic Electrochemistry [CHE-2002158]
- National Institutes of Health [GM-118176]
- Postdoctoral Fellowship for Research Abroad (JSPS)
- Experientia Foundation Fellowship
- Banting Postdoctoral Fellowship (NSERC)
- George E. Hewitt Foundation Fellowship for Medical Research
- National Institute of General Medical Sciences of the National Institutes of Health [K99GM140249]
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This translation discusses the importance of site-specific C-H bond oxidation in organic synthesis and the current limitations of chemical reagents in achieving this transformation. It introduces a platform using N-ammonium ylides as oxidants for site-specific, chemoselective C-H oxidation, which is guided by computation and can be applied to real-world problems in the agricultural and pharmaceutical sectors.
The site-specific oxidation of strong C(sp(3))-H bonds is of uncontested utility in organic synthesis. From simplifying access to metabolites and late-stage diversification of lead compounds to truncating retrosynthetic plans, there is a growing need for new reagents and methods for achieving such a transformation in both academic and industrial circles. One main drawback of current chemical reagents is the lack of diversity with regard to structure and reactivity that prevents a combinatorial approach for rapid screening to be employed. In that regard, directed evolution still holds the greatest promise for achieving complex C-H oxidations in a variety of complex settings. Herein we present a rationally designed platform that provides a step toward this challenge using N-ammonium ylides as electrochemically driven oxidants for site-specific, chemoselective C(sp(3))-H oxidation. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors.
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