Journal
CHEM
Volume 1, Issue 3, Pages 456-472Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2016.08.002
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Funding
- NIH NIGMS [R01-GM096129]
- Camille Dreyfus Teacher Scholar Award Program
- Eli Lilly and Co.
- University of Michigan
- Lilly Innovation Fellowship Award
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The direct trifluoromethylation of (hetero)arenes is a process of high importance to the pharmaceutical industry. Many reagents exist for this purpose and have found widespread use in discovery efforts; however, the step-intensive preparation of these reagents and their corresponding cost have resulted in minimal use of these methods in large-scale applications. For the ready transition of direct trifluoromethylation methodologies to large-scale application, the further development of processes utilizing inexpensive CF3 sources available on a metric ton scale is highly desirable. We report the use of pyridine N-oxide derivatives in concert with trifluoroacetic anhydride to promote a high-yielding and scalable trifluoromethylation reaction. Key mechanistic in-sights include the observation of electron donor-acceptor complexes in solution as well as a high dependence on photon flux. These observations have culminated in the application of this chemistry on a kilogram scale, demonstrating the utility of this reagent combination for preparative applications.
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