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From 2- to 3-Substituted Ferrocene Carboxamides or How to Apply Halogen "Dance" to the Ferrocene Series.
- Source :
-
Organometallics . 12/26/2017, Vol. 36 Issue 24, p4770-4778. 9p. - Publication Year :
- 2017
-
Abstract
- Two methods were compared to convert ferrocene into N,N-diisopropylferrocenecarboxamide, N,N-diethylferrocenecarboxamide, N,N-dimethylferrocenecarboxamide, and (4-morpholinocarbonyl)ferrocene, namely, deprotometalation followed by trapping using dialkylcarbamoyl chlorides and amide formation from the intermediate carboxylic acid. The four ferrocenecarboxamides were functionalized at C²; in the case of the less hindered and more sensitive amides, recourse to a mixed lithium-zinc 2,2,6,6-tetramethylpiperidino-based base allowed us to achieve the reactions. Halogen migration using lithium amides was next optimized. Whereas it appeared impossible to isolate the less hindered 3-iodoferrocenecarboxamides, 3-iodo-N,N-diisopropylferrocenecarboxamide proved stable and was converted to new 1,3-disubstituted ferrocenes by Suzuki coupling or amide reduction. DFT calculations were used to rationalize the results obtained. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 02767333
- Volume :
- 36
- Issue :
- 24
- Database :
- Academic Search Index
- Journal :
- Organometallics
- Publication Type :
- Academic Journal
- Accession number :
- 127025960
- Full Text :
- https://doi.org/10.1021/acs.organomet.7b00659