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Mild N‐Alkylation of Amines with Alcohols Catalyzed by the Acetate Ru(OAc) 2 (CO)(D i PPF) Complex
Author(s) -
Figliolia Rosario,
Baldino Salvatore,
Nedden Hans G.,
ZanottiGerosa Antonio,
Baratta Walter
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702996
Subject(s) - alkylation , catalysis , chemistry , medicinal chemistry , organic chemistry
The acetate complex Ru(OAc) 2 (D i PPF) ( 2 ) obtained from Ru(OAc) 2 (PPh 3 ) 2 ( 1 ) and 1,1′‐bis(diisopropylphosphino)ferrocene (D i PPF) reacts cleanly with formaldehyde affording Ru(OAc) 2 (CO)(D i PPF) ( 3 ) in high yield. The monocarbonyl complex 3 (0.4‐2 mol %) efficiently catalyzes the N‐alkylation of primary and secondary alkyl and aromatic amines using primary alcohols ROH (R=Et, n Pr, n Bu, PhCH 2 ) under mild reaction conditions (30–100 °C) with an alcohol/amine molar ratio of 10‐100. Formation of the monohydride RuH(OAc)(CO)(D i PPF) ( 4 ) has been observed by reaction of 3 with i PrOH in the presence of NEt 3 at RT through an equilibrium reaction.