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Arylation of Hydrocarbyl Ligands Formed from n ‐Alkanes through C–H Bond Activation of Benzene Using a Triruthenium Cluster
Author(s) -
Moriya Makoto,
Tahara Atsushi,
Takao Toshiro,
Suzuki Hiroharu
Publication year - 2009
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200900519
Subject(s) - chemistry , benzene , ligand (biochemistry) , linear alkylbenzene , yield (engineering) , pentane , medicinal chemistry , metal , alkylation , hydrogen bond , stereochemistry , photochemistry , organic chemistry , molecule , catalysis , pulmonary surfactant , biochemistry , materials science , receptor , metallurgy
Triruthenium complex 2 containing a perpendicularly coordinated 1‐pentyne ligand, which is one of the key intermediates of the reaction of triruthenium pentahydrido complex 1 with n ‐pentane, reacts with benzene to yield μ 3 ‐benzyne–μ 3 ‐pentylidyne complex 5 by C–H bond activation. β‐H elimination form the μ 3 ‐penytylidyne ligand occurred upon heating to yield μ 3 ‐pentenylidene complex 6 , which was followed by the formation of closo ‐ruthenacyclopentadiene complex 8 by the connection of the two hydrocarbyl moieties placed on each face of the triruthenium plane with partial metal–metal bond breaking. Treatment of 8 with pressurized hydrogen resulted in exclusive liberation of n ‐pentylbenzene, which is difficult to synthesize by conventional Friedel–Crafts alkylation. These sequential transformations correspond to the formation of linear alkylbenzene by the reaction of pentane with benzene on a trimetallic plane. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)