期刊
SCIENCE
卷 356, 期 6344, 页码 1272-1275出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aan1411
关键词
-
资金
- NSF [DGE 1106400, CHE-0840505]
- ARCS Foundation graduate research fellowship
- Swiss National Science Foundation
- National Institute of General Medical Sciences [R35 GM118190]
The biological properties of trifluoromethyl compounds have led to their ubiquity in pharmaceuticals, yet their chemical properties have made their preparation a substantial challenge, necessitating innovative chemical solutions. We report the serendipitous discovery of a borane-catalyzed formal C(sp(3))-CF3 reductive elimination from Au(III) that accesses these compounds by a distinct mechanism proceeding via fluoride abstraction, migratory insertion, and C-F reductive elimination to achieve a net C-C bond construction. The parent bis(trifluoromethyl) Au(III) complexes tolerate a surprising breadth of synthetic protocols, enabling the synthesis of complex organic derivatives without cleavage of the Au-C bond. This feature, combined with the fluoride-rebound mechanism, was translated into a protocol for the synthesis of F-18-radiolabeled aliphatic CF3-containing compounds, enabling the preparation of potential tracers for use in positron emission tomography.
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