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From 2- to 3-Substituted Ferrocene Carboxamides or How to Apply Halogen "Dance" to the Ferrocene Series.

Authors :
Tazi, Mehdi
Erb, William
Halauko, Yury S.
Ivashkevich, Oleg A.
Matulis, Vadim E.
Roisnel, Thierry
Dorcet, Vincent
Mongin, Florence
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