Ruthenium Carbene–Diether Ligand Complexes: Catalysts for Hydrogenation of Olefins
T Wang, C Pranckevicius, CL Lund, MJ Sgro… - …, 2013 - ACS Publications
T Wang, C Pranckevicius, CL Lund, MJ Sgro, DW Stephan
Organometallics, 2013•ACS PublicationsA series of carbene–diether ligands were prepared and the corresponding Ag salts used to
prepare the complexes RuHCl (PPh3) 2 (Im (OR) 2)(Im (OR) 2= C3H2 (NCH2CH2OR) 2; R=
Me (4a), t-Bu (4b), tert-hexyl (4c), Ph (4d), 2, 6-i-Pr2C6H3 (4e)). In an analogous fashion the
species RuHCl (PPh3) 2 (Y2Im (OMe) 2)(Y2Im (OMe) 2= Y2C3 (NCH2CH2OMe) 2; Y2=
C6H4 (4f), Y= Cl (4g), Me (4h)) were also synthesized. Similarly RuHCl (CO)(PPh3) 2 (Im
(OMe) 2)(5) was prepared and readily converted to RuHCl (CO)(SIMes)(Im (OMe) 2)(6) via …
prepare the complexes RuHCl (PPh3) 2 (Im (OR) 2)(Im (OR) 2= C3H2 (NCH2CH2OR) 2; R=
Me (4a), t-Bu (4b), tert-hexyl (4c), Ph (4d), 2, 6-i-Pr2C6H3 (4e)). In an analogous fashion the
species RuHCl (PPh3) 2 (Y2Im (OMe) 2)(Y2Im (OMe) 2= Y2C3 (NCH2CH2OMe) 2; Y2=
C6H4 (4f), Y= Cl (4g), Me (4h)) were also synthesized. Similarly RuHCl (CO)(PPh3) 2 (Im
(OMe) 2)(5) was prepared and readily converted to RuHCl (CO)(SIMes)(Im (OMe) 2)(6) via …
A series of carbene–diether ligands were prepared and the corresponding Ag salts used to prepare the complexes RuHCl(PPh3)2(Im(OR)2) (Im(OR)2 = C3H2(NCH2CH2OR)2; R = Me (4a), t-Bu (4b), tert-hexyl (4c), Ph (4d), 2,6-i-Pr2C6H3 (4e)). In an analogous fashion the species RuHCl(PPh3)2(Y2Im(OMe)2) (Y2Im(OMe)2 = Y2C3(NCH2CH2OMe)2; Y2 = C6H4 (4f), Y = Cl (4g), Me (4h)) were also synthesized. Similarly RuHCl(CO)(PPh3)2(Im(OMe)2) (5) was prepared and readily converted to RuHCl(CO)(SIMes)(Im(OMe)2) (6) via treatment with SIMes. The reaction of 4a with SIMes afforded RuHCl(SIMes)(Im(OMe)2)(PPh3) (7), which reacts subsequently with Na[BPh4] to give [RuH(Im(OMe)2)(SIMes)][(η6-Ph)BPh3] (8). In a series of tests, the species 4a–h, 5, 6, and 8 were shown to catalyze the hydrogenations of 1-hexene, cyclohexene, and dimethyl itaconate. From the activity of 4a–h it is clear that the capability of the carbene–ether substituents to coordinate to the metal as well as electron-donating substituents on the carbene fragment enhances catalytic activity. Other variations such as in 5, 6, and 8 resulted in terminal-olefin-selective hydrogenation catalysts, although the zwitterionic species 8 showed significantly enhanced activity.
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