Journal
ISRAEL JOURNAL OF CHEMISTRY
Volume 57, Issue 10-11, Pages 1037-1046Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ijch.201700099
Keywords
Ruthenium; C-H Activation; Olefin Hydroarylation; Ethylbenzene; Styrene
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Funding
- U.S. Department of Energy, Office of Basic Energy Sciences [DE-SC0000776, DE-FG02-03ER15387]
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The complex [(MeOTTM)Ru(P(OCH2)(3)CEt)(NCMe) Ph][BAr4'] (MeOTMM= 4,4', 4 ''-(methoxymethanetriyl)-tris(1-benzyl-1H-1,2,3-triazole), BAr4'= tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) is used to catalyze the hydrophenylation of ethylene to produce styrene and ethylbenzene. The selectivity of styrene versus ethylbenzene varies as a function of ethylene pressure, and replacing the MeOTTM ligand with tris(1-phenyl-1H-1,2,3-triazol-4-yl)methanol reduces the selectivity toward styrene. For styrene production ethylene serves as the oxidant to produce ethane, as determined by both H-1 NMR spectroscopy and GC-MS. The Ru(III/II) potentials of [(MeOTTM)Ru[P(OCH2)(3)CEt](NCMe)Ph][BAr4'] (0.86 V) and [(HC(pz(5))(3))Ru[P(OCH2)(3)CEt](NCMe)Ph][BA(4)'] (0.82 V) (HC(pz(5))(3)=tris(5-methyl-pyrazolyl)methane) are nearly identical. Since catalytic conversion of ethylene and benzene by [(HC(pz(5))(3))Ru[P(OCH2)(3)CEt](NCMe)Ph][BAr4'] is known to selectively produce ethylbenzene, the formation of styrene using [(MeOTTM)Ru[P(OCH2)(3)CEt](NCMe) Ph][BAr4'] is attributed to the substituents on the triazole rings of the MeOTTM ligand.
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