BIOMAT Database Logo BIOMAT Database Logo

Dialkylamino cyclopentadienyl ruthenium(ii) complex-catalyzed alpha-alkylation of arylacetonitriles with primary alcohols. 2010

Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, People's Republic of China.

Aminocyclopentadienyl ruthenium complexes, [(eta(5)-C(5)H(4)NMe(2))Ru(PPh(3))(2)(CH(3)CN)](+)BF(4)(-) and [(eta(5)-C(5)H(4)NEt(2))Ru(PPh(3))(2)(CH(3)CN)](+)BF(4)(-), are moderately active catalysts for alpha-alkylation of arylacetonitriles with primary alcohols; on the other hand, the analogous unsubstituted cyclopentadienyl ruthenium complex [(eta(5)-C(5)H(5))Ru(PPh(3))(2)(CH(3)CN)](+)BF(4)(-) shows very low catalytic activity. On the basis of experimental results and theoretical calculations, rationalization for the much higher catalytic activity of the aminocyclopentadienyl complexes over that of the unsubstituted Cp complex is provided. In the catalytic systems with the former, it is possible to regenerate the active solvento complexes via protonation of the metal hydride intermediates and subsequent ligand substitution; this process is, however, very nonfacile in the catalytic system with the latter.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D006841 Hydrocarbons, Aromatic Organic compounds containing carbon and hydrogen in the form of an unsaturated, usually hexagonal ring structure. The compounds can be single ring, or double, triple, or multiple fused rings. Aromatic Hydrocarbon,Aromatic Hydrocarbons,Hydrocarbon, Aromatic
D000097 Acetonitriles Compounds in which a methyl group is attached to the cyano moiety. Cyanomethane,Cyanomethanes,Ethane Nitriles,Methyl Cyanide,Methyl Cyanides,Cyanide, Methyl,Cyanides, Methyl,Nitriles, Ethane
D000438 Alcohols Alkyl compounds containing a hydroxyl group. They are classified according to relation of the carbon atom: primary alcohols, R-CH2OH; secondary alcohols, R2-CHOH; tertiary alcohols, R3-COH. (From Grant & Hackh's Chemical Dictionary, 5th ed)
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations
D017975 Ruthenium Compounds Inorganic compounds that contain ruthenium as an integral part of the molecule. Compounds, Ruthenium

Related Publications

Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Nickel-Catalyzed α-Alkylation of Arylacetonitriles with Challenging Secondary Alcohols.
January 2023, The Journal of organic chemistry,
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Ruthenium-catalyzed alkylation of oxindole with alcohols.
May 2009, The Journal of organic chemistry,
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Base-Promoted α-Alkylation of Arylacetonitriles with Alcohols.
July 2019, Chemistry, an Asian journal,
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
α-Alkylation of arylacetonitriles with primary alcohols catalyzed by backbone modified N-heterocyclic carbene iridium(I) complexes.
February 2021, Dalton transactions (Cambridge, England : 2003),
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Efficient α-Alkylation of Arylacetonitriles with Secondary Alcohols Catalyzed by a Phosphine-Free Air-Stable Iridium(III) Complex.
December 2020, The Journal of organic chemistry,
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Enantio- and diastereoselective asymmetric allylic alkylation catalyzed by a planar-chiral cyclopentadienyl ruthenium complex.
July 2015, Chemical communications (Cambridge, England),
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Iridium-catalyzed alpha-alkylation of acetates with primary alcohols and diols.
March 2010, Journal of the American Chemical Society,
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Selective alkylation of (hetero)aromatic amines with alcohols catalyzed by a ruthenium pincer complex.
March 2012, Organic letters,
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
Direct beta-alkylation of secondary alcohols with primary alcohols catalyzed by a CpIr complex.
September 2005, Organic letters,
Hung Wai Cheung, and Juan Li, and Wenxu Zheng, and Zhongyuan Zhou, and Yu Hin Chiu, and Zhenyang Lin, and Chak Po Lau
NNN Pincer Ru(II)-Complex-Catalyzed α-Alkylation of Ketones with Alcohols.
April 2018, The Journal of organic chemistry,
Copied contents to your clipboard!