C-H fluorination of heterocycles with silver (II) fluoride
US9701635B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Jul 28, 2014 |
| Grant date | Jul 11, 2017 |
| Priority date | — |
| Expiry date | Oct 18, 2034 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D405/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention provides compositions and methods for the selective C—H fluorination of nitrogen-containing heteroarenes with AgF2, which has previously been considered too reactive for practical, selective C—H fluorination. Fluorinated heteroarenes are prevalent in numerous pharmaceuticals, agrochemicals and materials. However, the reactions used to introduce fluorine into these molecules require pre-functionalized substrates or the use of F2 gas. The present invention provides a mild and general method for the C—H fluorination of nitrogen-containing heteroarene compounds to 2-fluoro-heteroarenes with commercially available AgF2. In various embodiments, these reactions occur at ambient temperature within one hour and occur with exclusive selectivity for fluorination at the 2-position. Exemplary reaction conditions are effective for fluorinating diazine heteroarenes to form a single fluorinated isomer.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.