Homogeneous asymmetric hydrogenation of o-substituted acetophenones catalyzed by NH2Et2{Ru2Cl5[(S)-tol-BINAP]2}

Rui-Xiang Li; Pu-Ming Cheng; Dong-Wen Li; Hua Chen; Xian-Jun Li; Carl Wessman; Ning-Bew Wong; Kam-Chung Tin

doi:10.1016/S1381-1169(00)00188-6

Homogeneous asymmetric hydrogenation of o-substituted acetophenones catalyzed by NH₂Et₂{Ru₂Cl₅[(S)-tol-BINAP]₂}

Rui-Xiang Li
, Pu-Ming Cheng
, Dong-Wen Li
, Hua Chen
, Xian-Jun Li
, Carl Wessman
, Ning-Bew Wong
, Kam-Chung Tin

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

9 Citations (Scopus)

Abstract

Acetophenones o-substituted by halogen and methoxyl groups were hydrogenated in the presence of (NH₂Et₂){Ru₂Cl₅[(S)-tol-BINAP]₂} at 35°C and 85 kg/cm² hydrogen pressure. The results showed that o-bromoacetophenone was a very active substrate and its asymmetric hydrogenation gave an o-bromo-α-phenylethanol with very high enantioselectivity (97% ee). o-Chloroacetophenone was moderately active and its hydrogenation product o-chloro-α-phenyl-ethanol had a good enantioselectivity (82% ee). o-Fluoroacetophenone exhibited a low reactivity but its hydrogenation product o-fluoro-α-phenylethanol showed the highest enantioselectivity (99% ee) among all products, o-Methoxyace-tophenone showed a low reactivity, and its hydrogenation product o-methoxyl-α-phenylethanol gave a low enantioselectivity (27% ee). The effects of various reaction conditions, such as hydrogen pressure, reaction temperature, solvents, reaction time, ligand concentration and addition of acid and base, were investigated. (C) 2000 Elsevier Science B.V.

Original language	English
Pages (from-to)	179-184
Journal	Journal of Molecular Catalysis A: Chemical
Volume	159
Issue number	2
DOIs	https://doi.org/10.1016/S1381-1169(00)00188-6
Publication status	Published - 2 Oct 2000

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

Research Keywords

(S)-tol-BINAP
o-substituted acetophenone
Ruthenium

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10.1016/S1381-1169(00)00188-6

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@article{7c6203c8311145d385eb366791212dd0,

title = "Homogeneous asymmetric hydrogenation of o-substituted acetophenones catalyzed by NH2Et2\{Ru2Cl5[(S)-tol-BINAP]2\}",

abstract = "Acetophenones o-substituted by halogen and methoxyl groups were hydrogenated in the presence of (NH2Et2)\{Ru2Cl5[(S)-tol-BINAP]2\} at 35°C and 85 kg/cm2 hydrogen pressure. The results showed that o-bromoacetophenone was a very active substrate and its asymmetric hydrogenation gave an o-bromo-α-phenylethanol with very high enantioselectivity (97\% ee). o-Chloroacetophenone was moderately active and its hydrogenation product o-chloro-α-phenyl-ethanol had a good enantioselectivity (82\% ee). o-Fluoroacetophenone exhibited a low reactivity but its hydrogenation product o-fluoro-α-phenylethanol showed the highest enantioselectivity (99\% ee) among all products, o-Methoxyace-tophenone showed a low reactivity, and its hydrogenation product o-methoxyl-α-phenylethanol gave a low enantioselectivity (27\% ee). The effects of various reaction conditions, such as hydrogen pressure, reaction temperature, solvents, reaction time, ligand concentration and addition of acid and base, were investigated. (C) 2000 Elsevier Science B.V.",

keywords = "(S)-tol-BINAP, o-substituted acetophenone, Ruthenium",

author = "Rui-Xiang Li and Pu-Ming Cheng and Dong-Wen Li and Hua Chen and Xian-Jun Li and Carl Wessman and Ning-Bew Wong and Kam-Chung Tin",

note = "Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].",

year = "2000",

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doi = "10.1016/S1381-1169(00)00188-6",

language = "English",

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pages = "179--184",

journal = "Journal of Molecular Catalysis A: Chemical",

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TY - JOUR

T1 - Homogeneous asymmetric hydrogenation of o-substituted acetophenones catalyzed by NH2Et2{Ru2Cl5[(S)-tol-BINAP]2}

AU - Li, Rui-Xiang

AU - Cheng, Pu-Ming

AU - Li, Dong-Wen

AU - Chen, Hua

AU - Li, Xian-Jun

AU - Wessman, Carl

AU - Wong, Ning-Bew

AU - Tin, Kam-Chung

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

PY - 2000/10/2

Y1 - 2000/10/2

N2 - Acetophenones o-substituted by halogen and methoxyl groups were hydrogenated in the presence of (NH2Et2){Ru2Cl5[(S)-tol-BINAP]2} at 35°C and 85 kg/cm2 hydrogen pressure. The results showed that o-bromoacetophenone was a very active substrate and its asymmetric hydrogenation gave an o-bromo-α-phenylethanol with very high enantioselectivity (97% ee). o-Chloroacetophenone was moderately active and its hydrogenation product o-chloro-α-phenyl-ethanol had a good enantioselectivity (82% ee). o-Fluoroacetophenone exhibited a low reactivity but its hydrogenation product o-fluoro-α-phenylethanol showed the highest enantioselectivity (99% ee) among all products, o-Methoxyace-tophenone showed a low reactivity, and its hydrogenation product o-methoxyl-α-phenylethanol gave a low enantioselectivity (27% ee). The effects of various reaction conditions, such as hydrogen pressure, reaction temperature, solvents, reaction time, ligand concentration and addition of acid and base, were investigated. (C) 2000 Elsevier Science B.V.

AB - Acetophenones o-substituted by halogen and methoxyl groups were hydrogenated in the presence of (NH2Et2){Ru2Cl5[(S)-tol-BINAP]2} at 35°C and 85 kg/cm2 hydrogen pressure. The results showed that o-bromoacetophenone was a very active substrate and its asymmetric hydrogenation gave an o-bromo-α-phenylethanol with very high enantioselectivity (97% ee). o-Chloroacetophenone was moderately active and its hydrogenation product o-chloro-α-phenyl-ethanol had a good enantioselectivity (82% ee). o-Fluoroacetophenone exhibited a low reactivity but its hydrogenation product o-fluoro-α-phenylethanol showed the highest enantioselectivity (99% ee) among all products, o-Methoxyace-tophenone showed a low reactivity, and its hydrogenation product o-methoxyl-α-phenylethanol gave a low enantioselectivity (27% ee). The effects of various reaction conditions, such as hydrogen pressure, reaction temperature, solvents, reaction time, ligand concentration and addition of acid and base, were investigated. (C) 2000 Elsevier Science B.V.

KW - (S)-tol-BINAP

KW - o-substituted acetophenone

KW - Ruthenium

UR - https://www.scopus.com/pages/publications/0034597069

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U2 - 10.1016/S1381-1169(00)00188-6

DO - 10.1016/S1381-1169(00)00188-6

M3 - RGC 21 - Publication in refereed journal

SN - 1381-1169

VL - 159

SP - 179

EP - 184

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

IS - 2

ER -