期刊
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
卷 108, 期 35, 页码 14411-14415出版社
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1109059108
关键词
medicinal chemistry; C-H functionalization; synthetic methodology
资金
- National Institutes of Health/National Institute of General Medical Sciences [GM-073949]
- Ministerio de Eduacion y Ciencia
- Deutscher Akademischer Austauschdienst
- National Science Foundation
- Japan Society for the Promotion of Science
- Amgen
- Bristol-Myers Squibb
Direct methods for the trifluoromethylation of heteroaromatic systems are in extremely high demand in nearly every sector of chemical industry. Here we report the discovery of a general procedure using a benchtop stable trifluoromethyl radical source that functions broadly on a variety of electron deficient and rich heteroaromatic systems and demonstrates high functional group tolerance. This C-H trifluoromethylation protocol is operationally simple (avoids gaseous CF3I), scalable, proceeds at ambient temperature, can be used directly on unprotected molecules, and is demonstrated to proceed at the innately reactive positions of the substrate. The unique and orthogonal reactivity of the trifluoromethyl radical relative to aryl radicals has also been investigated on both a complex natural product and a pharmaceutical agent. Finally, preliminary data suggest that the regioselectivity of C-H trifluoromethylation can be fine-tuned simply by judicious solvent choice.
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