C-scorpionate iron(II) complexes as highly selective catalysts for the hydrocarboxylation of cyclohexane

[Display omitted] •Homogeneous C-scorpionate Fe(II) complex catalyze cyclohexane hydrocarboxylation.•Water acts as a source of the hydroxide moiety in the carboxylic acid group.•Cyclohexanecarboxylic acid is selectively produced in good yield. The C-scorpionate iron(II) complexes [FeCl2{κ3-HC(pz)3}]...

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Bibliographic Details
Published in:Inorganica Chimica Acta 2019-04, Vol.489, p.269-274
Main Authors: Matias, Inês A.S., Ribeiro, Ana P.C., Alegria, Elisabete C.B.A., Pombeiro, Armando J.L., Martins, Luísa M.D.R.S.
Format: Article
Language:English
Subjects:
Alkanes
Aqueous medium
Carboxylic acid
Catalysis
Catalysts
Coordination compounds
Cyclohexane
Homogeneous catalysis
Hydrocarboxylation
Iron
Iron chlorides
Scorpionate
Selectivity
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Summary:[Display omitted] •Homogeneous C-scorpionate Fe(II) complex catalyze cyclohexane hydrocarboxylation.•Water acts as a source of the hydroxide moiety in the carboxylic acid group.•Cyclohexanecarboxylic acid is selectively produced in good yield. The C-scorpionate iron(II) complexes [FeCl2{κ3-HC(pz)3}] (1) (pz = pyrazol-1-yl), Li[FeCl2{κ3-SO3C(pz)3}] (2) and the new [FeCl2{κ3-HOCH2C(pz)3}] (3) act as catalysts for the hydrocarboxylation of cyclohexane (with CO and H2O) to cyclohexanecarboxylic acid in a remarkable yield (up to 60%) and under mild conditions. The catalysts selectivity for the acid can be tuned by CO pressure, catalyst amount and reaction temperature. Complex [FeCl2{κ3-HC(pz)3}] (1) provides the most effective catalyst requiring low CO pressure. This work constitutes an unprecedented use of iron complexes as catalysts for the hydrocarboxylation of alkanes.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2019.02.035