Hydroamination of 2-vinylpyridine, styrene, and isoprene with pyrrolidine catalyzed by alkali and alkaline-earth metal complexes

• Published in: Russian chemical bulletin Vol. 65; no. 12; pp. 2887 - 2894
• Main Authors: Yakub, A. M., Moskalev, M. V., Bazyakina, N. L., Cherkasov, A. V., Shavyrin, A. S., Fedushkin, I. L.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-12-2016; Springer Nature B.V
• Subjects: Alkaline earth metals; Anions; Calcium; Catalysts; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Coordination compounds; Full Articles; Inorganic Chemistry; Isoprene; Lithium; Magnesium; Organic Chemistry; Room temperature; Sodium; Sodium salts; Styrenes; alkenes; group 1 and 2 metals; hydroamination
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-016-1673-8

The complexes (dpp-bian)Mg(thf)
3
, (dpp-bian)Ca(thf)
4
and (dpp-bian)Mg(pyr)
3
(dpp-bian is the 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene dianion; pyr is the pyrrolidine) catalyze the addition of pyrrolidine to 2-vinylpyridine at room temperature. The compound (dppbian)Mg[N(SiMe
3
)
2
] containing a dpp-bian radical anion catalyzes the addition of pyrrolidine to styrene at 60 °C. The dpp-bian radical anion lithium-sodium salt [(dpp-bian)Li{N-(SiMe
3
)
2
}][Na(C
7
H
8
)] is an active catalyst of the addition of pyrrolidine to styrene and isoprene at 60 °C. In all the case, the content of the catalyst was from 1 to 2 mol.%. For styrene and 2-vinylpyridine, the reactions proceeded with the formation of anti-Markovnikov addition product, while 1,4-addition product was obtained in the case of isoprene.