Ring lithiation and functionalization of imidazol-2-ylidene-boranes
Organic Letters, ISSN: 1523-7060, Vol: 13, Issue: 22, Page: 6042-6045
2011
- 17Citations
- 21Captures
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Metrics Details
- Citations17
- Citation Indexes17
- CrossRef17
- 17
- Captures21
- Readers21
- 21
Article Description
N,N′-Dialkyl and N,N′-diaryl imidazol-2-ylidene-boranes and trifluoroboranes are rapidly lithiated at C4 of the imidazole ring, and the resulting intermediates have been quenched with an assortment of electrophiles to provide ring-functionalized imidazol-2-ylidene-boranes. Further deprotonation and functionalization of C5 have been demonstrated. Deboronation of the products by treatment with triflic acid or iodine and then methanol opens a route to C4/C5 functionalized imidazolium salts and imidazol-2-ylidenes. © 2011 American Chemical Society.
Bibliographic Details
American Chemical Society (ACS)
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