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Title: Catalytic ionic hydrogenation of ketones using tungsten or molybdenum organometallic species

Abstract

The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes. The functional group is selected from groups represented by the formulas R(C.dbd.O)R' and R(C.dbd.O)H, wherein R and R' are selected from hydrogen or any alkyl or aryl group. The active catalyst for the process has the form: [CpM(CO).sub.2 (PR*.sub.3) L].sup.+ A.sup.-, where Cp=.eta..sup.5 -R.sup..tangle-solidup..sub.m C.sub.5 H.sub.5-m and R.sup..tangle-solidup. represents an alkyl group or a halogen (F, Cl, Br, I) or R.sup..tangle-solidup. =OR' (where R'=H, an alkyl group or an aryl group) or R.sup..tangle-solidup. =CO.sub.2 R' (where R'=H, an alkyl group or an aryl group) and m=0 to 5; M represents a molybdenum atom or a tungsten atom; R*.sub.3 represents three hydrocarbon groups selected from a cyclohexyl group (C.sub.6 H.sub.11), a methyl group (CH.sub.3), and a phenyl group (C.sub.6 H.sub.5) and all three R* groups can be the same or different or two of the three groups can be the same; L represents a ligand; and A.sup.- represents an anion. In another embodiment, one, two or three of the R* groups can be an OR*.

Inventors:
 [1];  [2]
  1. Leverkusen, DE
  2. Wading River, NY
Issue Date:
Research Org.:
Brookhaven National Laboratory (BNL), Upton, NY (United States)
OSTI Identifier:
873265
Patent Number(s):
6124509
Assignee:
Brookhaven Science Associates (Upton, NY)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
DOE Contract Number:  
AC02-98CH10886
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
catalytic; ionic; hydrogenation; ketones; tungsten; molybdenum; organometallic; species; process; aldehydes; alcohols; temperatures; pressures; complexes; functional; selected; represented; formulas; dbd; hydrogen; alkyl; aryl; active; catalyst; form; cpm; cp; eta; -r; tangle-solidup; 5-m; represents; halogen; br; atom; hydrocarbon; cyclohexyl; 11; methyl; phenyl; ligand; anion; embodiment; active catalyst; catalytic hydrogenation; metallic species; /999/

Citation Formats

Voges, Mark, and Bullock, R Morris. Catalytic ionic hydrogenation of ketones using tungsten or molybdenum organometallic species. United States: N. p., 2000. Web.
Voges, Mark, & Bullock, R Morris. Catalytic ionic hydrogenation of ketones using tungsten or molybdenum organometallic species. United States.
Voges, Mark, and Bullock, R Morris. Sat . "Catalytic ionic hydrogenation of ketones using tungsten or molybdenum organometallic species". United States. https://www.osti.gov/servlets/purl/873265.
@article{osti_873265,
title = {Catalytic ionic hydrogenation of ketones using tungsten or molybdenum organometallic species},
author = {Voges, Mark and Bullock, R Morris},
abstractNote = {The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes. The functional group is selected from groups represented by the formulas R(C.dbd.O)R' and R(C.dbd.O)H, wherein R and R' are selected from hydrogen or any alkyl or aryl group. The active catalyst for the process has the form: [CpM(CO).sub.2 (PR*.sub.3) L].sup.+ A.sup.-, where Cp=.eta..sup.5 -R.sup..tangle-solidup..sub.m C.sub.5 H.sub.5-m and R.sup..tangle-solidup. represents an alkyl group or a halogen (F, Cl, Br, I) or R.sup..tangle-solidup. =OR' (where R'=H, an alkyl group or an aryl group) or R.sup..tangle-solidup. =CO.sub.2 R' (where R'=H, an alkyl group or an aryl group) and m=0 to 5; M represents a molybdenum atom or a tungsten atom; R*.sub.3 represents three hydrocarbon groups selected from a cyclohexyl group (C.sub.6 H.sub.11), a methyl group (CH.sub.3), and a phenyl group (C.sub.6 H.sub.5) and all three R* groups can be the same or different or two of the three groups can be the same; L represents a ligand; and A.sup.- represents an anion. In another embodiment, one, two or three of the R* groups can be an OR*.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Sat Jan 01 00:00:00 EST 2000},
month = {Sat Jan 01 00:00:00 EST 2000}
}

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journal, March 1997


Group 6 anionic μ-hydride complexes [HM2(CO)10]− (M = Cr, Mo, W): New catalysts for hydrogenation and hydrosilylation
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Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using a Formic Acid−Triethylamine Mixture
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Homogeneous hydrogenation of ketones using chromium hexacarbonyl as catalyst precursor in the presence of bases
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Homogeneous Transfer Hydrogenation of Ketones Catalyzed by Molybdenum Complexes
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Homogeneous asymmetric hydrogenation of functionalized ketones
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Practical Enantioselective Hydrogenation of Aromatic Ketones
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Anionic group 6 hydrides and carboxylates as homogeneous catalysts for reduction of aldehydes and ketones
journal, September 1986


Asymmetric hydrogenation of cycloalkanones catalyzed by BINAP-iridium(I)-aminophosphine systems
journal, April 1993


Hydride Transfer by Hydrido Transition-Metal Complexes. Ionic Hydrogenation of Aldehydes and Ketones, and Structural Characterization of an Alcohol Complex
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