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Catalysis of linear alkene metathesis by Grubbs-type ruthenium alkylidene complexes containing hemilabile α,α-diphenyl-(monosubstituted-pyridin-2-yl)methanolato ligands

Tegene T. Tole, Johan H. L. Jordaan and Hermanus C. M. Vosloo

Beilstein J. Org. Chem. 2019, 15, 194–209. https://doi.org/10.3762/bjoc.15.19

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Tegene T. Tole, Johan H. L. Jordaan and Hermanus C. M. Vosloo

Beilstein J. Org. Chem. 2019, 15, 194–209. https://doi.org/10.3762/bjoc.15.19

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Tole, T. T.; Jordaan, J. H. L.; Vosloo, H. C. M. Beilstein J. Org. Chem. 2019, 15, 194–209. doi:10.3762/bjoc.15.19

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TY  - JOUR
A1  - Tole, Tegene T.
A1  - Jordaan, Johan H. L.
A1  - Vosloo, Hermanus C. M.
T1  - Catalysis of linear alkene metathesis by Grubbs-type ruthenium alkylidene complexes containing hemilabile α,α-diphenyl-(monosubstituted-pyridin-2-yl)methanolato ligands
JF  - Beilstein Journal of Organic Chemistry
PY  - 2019///
VL  - 15
SP  - 194
EP  - 209
SN  - 1860-5397
DO  - 10.3762/bjoc.15.19
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.15.19
KW  - Grubbs-type precatalyst
KW  - hemilabile
KW  - 1-octene metathesis
KW  - pyridinyl-alcoholato ligand
N2  - Four new Grubbs-type precatalysts [RuCl(H2IMes)(O^N)(=CHPh)], where [O^N = α,α-diphenyl-(3-methylpyridin-2-yl)methanolato, α,α-diphenyl-(4-methylpyridin-2-yl)methanolato, α,α-diphenyl-(5-methylpyridin-2-yl)methanolato and α,α-diphenyl-(3-methoxypyridin-2-yl)methanolato] were synthesized and tested for their activity, stability and selectivity in the 1-octene metathesis reaction. Overall the precatalysts showed good activity and high stability for the metathesis of 1-octene at temperatures above 80 °C and up to 110 °C. Selectivities towards the primary metathesis products, i.e., 7-tetradecene and ethene, above 85% were obtained with all the precatalysts at 80 and 90 °C. High selectivities were also observed at 100 °C for the 4-Me- and 3-OMe-substituted precatalysts. With an increase in temperature an increase in isomerisation products and secondary metathesis products were observed with the latter reaching values >20% for the 3-OMe- and 3-Me-substituted precatalysts at 110 and 100 °C, respectively. All the precatalysts exhibits first-order kinetics at 80 °C with the 3-substituted precatalysts the slowest. The behaviour of the 3-substituted precatalysts can be attributed to electronic and steric effects associated with the adjacent bulky phenyl groups.
ER  -

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Scholarly Works

Edor, J.; Joseph, M.; Jordaan, J.; Vosloo, H.; Swarts, A. Formic Acid Dehydrogenation Catalysis Using Novel Pyridyl‐Formamidine Half‐Sandwich Ruthenium(II) Complexes. Applied Organometallic Chemistry 2025, 39. doi:10.1002/aoc.70016

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