skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Efficient carbon-supported heterogeneous molybdenum-dioxo catalyst for chemoselective reductive carbonyl coupling

Journal Article · · Catalysis Science and Technology
DOI:https://doi.org/10.1039/c7cy00336f· OSTI ID:1871002
 [1];  [1];  [1];  [2]; ORCiD logo [1]; ORCiD logo [1]
  1. Northwestern Univ., Evanston, IL (United States)
  2. Northwestern Univ., Evanston, IL (United States); Argonne National Lab. (ANL), Argonne, IL (United States)
+ Show Author Affiliations

Reductive coupling of various carbonyl compounds to the corresponding symmetric ethers with dimethylphenylsilane is reported using a carbon-supported dioxo-molybdenum catalyst. The catalyst is air- and moisture-stable and can be easily separated from the reaction mixture for recycling. In addition, the catalyst is chemoselective, thus enabling the synthesis of functionalized ethers without requiring sacrificial ligands or protecting groups.

Research Organization:
Northwestern Univ., Evanston, IL (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
DOE Contract Number:
FG02-03ER15457; CHE-1048773; CHE-9871268; DMR-0521267; DMR-1121262; NNCI-1542205; CHE-1213235
OSTI ID:
1871002
Journal Information:
Catalysis Science and Technology, Vol. 7, Issue 11; ISSN 2044-4753
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English

References (50)

Palladium Alkoxides:  Potential Intermediacy in Catalytic Amination, Reductive Elimination of Ethers, and Catalytic Etheration. Comments on Alcohol Elimination from Ir(III) journal January 1996
Synthesis and Structure−Activity Relationships of Trisubstituted Phenyl Urea Derivatives as Neuropeptide Y5 Receptor Antagonists journal June 2001
Synthesis of ethers from esters via Fe-catalyzed hydrosilylation journal January 2012
Handbook of Heterogeneous Catalysis book March 2008
Ueber die Theorie der Aetherbildung journal January 1851
XXII.—On etherification journal January 1852
Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine journal May 1998
Advances in Base-Metal-Catalyzed Alkene Hydrosilylation journal January 2017
Reactions of Hydrosilanes with Transition Metal Complexes journal August 2016
Catalyzing Aldehyde Hydrosilylation with a Molybdenum(VI) Complex: A Density Functional Theory Study journal May 2007
Mechanism of the MoO 2 Cl 2 -Catalyzed Hydrosilylation:  A DFT Study journal November 2007
New aryl/heteroaryl CN bond cross-coupling reactions via arylboronic acid/cupric acetate arylation journal May 1998
Reaction of acetals and trialkylsilanes catalyzed by trimethylsilyl trifluoromethanesulfonate. A simple method for conversion of acetals to ethers journal January 1979
General ether synthesis under mild acid-free conditions. Trimethylsilyl iodide catalyzed reductive coupling of carbonyl compounds with trialkylsilanes to symmetrical ethers and reductive condensation with alkoxysilanes to unsymmetrical ethers journal September 1987
Carbon−Heteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides journal December 1998
Synthesis of Oxygen Heterocycles via a Palladium-Catalyzed C−O Bond-Forming Reaction journal January 1996
Catalysis of esterification reactions by oxo-molybdenum-alkoxides: X-ray structures of Cl2(O)Mo(μ-nPr)2(μ-HOnPr)Mo(O)Cl2 and Cl2(O)Mo(μ-OEt)2(μ2-η1η1-HOCH2CH2OH)Mo(O)Cl2 journal November 1998
Olefin Hydroaryloxylation Catalyzed by Pincer–Iridium Complexes journal September 2013
Reductive etherification of carbonyl compounds with alkyl trimethylsilylethers using polymethylhydrosiloxane (PMHS) and catalytic B(C 6 F 5 ) 3 journal July 2004
A Novel Method for the Preparation of Symmetrical and Unsymmetrical Ethers. Trityl Perchlorate Promoted Reduction of Carbonyl Compounds with Triethylsilane journal June 1985
[MoO 2 Cl 2 ] as catalyst for hydrosilylation of aldehydes and ketones journal January 2005
Efficient catalytic greenhouse gas-free hydrogen and aldehyde formation from aqueous alcohol solutions journal January 2017
Hidden Brønsted Acid Catalysis: Pathways of Accidental or Deliberate Generation of Triflic Acid from Metal Triflates journal November 2011
Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative Annulation at Unactivated Terminal Positions journal September 2015
Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O-, S-, and N-Nucleophiles journal September 2011
Reactivity of a Carbon-Supported Single-Site Molybdenum Dioxo Catalyst for Biodiesel Synthesis journal September 2016
Electronic Structure of the Hydroxo and Methoxo Oxometalate Anions MO 3 (OH) - and MO 3 (OCH 3 ) - (M = Cr, Mo, and W) journal December 2005
Phenomena Affecting Catalytic Reactions at Solid–Liquid Interfaces journal November 2016
New N- and O-arylations with phenylboronic acids and cupric acetate journal May 1998
Trimethylsilyl Iodide Catalyzed Reductive Coupling of Aldehydes with Tertiary Alkoxytrimethylsilanes to Crowded Unsymmetrical Ethers 1 journal January 1992
Antimony( v ) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes journal January 2016
Catalysis by transition metal complexes of alkene silylation–recent progress and mechanistic implications journal November 2005
Copper(I) Phenoxide Complexes in the Etherification of Aryl Halides journal March 2010
Recent Developments in the Synthesis of Supported Catalysts journal June 2015
High-valent oxo-molybdenum and oxo-rhenium complexes as efficient catalysts for X–H (X = Si, B, P and H) bond activation and for organic reductions journal January 2012
Surface Organometallic and Coordination Chemistry toward Single-Site Heterogeneous Catalysts: Strategies, Methods, Structures, and Activities journal January 2016
Dioxomolybdenum( vi ) complexes as catalysts for the hydrosilylation of aldehydes and ketones journal January 2006
Preparation of Esters of Phosphoric Acid by the Reaction of Trivalent Phosphorus Compounds with Diethyl Azodicarboxylate in the Presence of Alcohols journal April 1967
Expanding the role of oxo-molybdenum(vi) catalysts: a DFT interpretation of X–H activation leading to reduction or oxidation journal January 2009
Palladium-Catalyzed Intermolecular Carbon−Oxygen Bond Formation:  A New Synthesis of Aryl Ethers journal April 1997
Silane reductions in acidic media. I. Reduction of aldehydes and ketones in alcoholic acidic media. General synthesis of ethers journal May 1972
Selective homogeneous synthesis of dimethyl ether from methanol journal January 2010
Synthesis of Diaryl Ethers: A Long-Standing Problem Has Been Solved journal August 1999
Hydrosilylation reaction of olefins: recent advances and perspectives journal January 2015
Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts journal October 1967
Enantioselective Allylic Etherification: Selective Coupling of Two Unactivated Alcohols journal May 2011
Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols journal June 2010
Influence of Lewis Acid and Solvent in the Hydrosilylation of Aldehydes and Ketones with Et3SiH; Tris(pentafluorophenyl)borane B(C6F5)3 versus Metal Triflates [M(OTf)3; M = Sc, Bi, Ga, and Al] - Mechanistic Implications journal February 2009
Siloxycarbenium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borates and Their Role in Reactions of Ketones with Nucleophiles journal April 1992
Gold(I)-Catalyzed Intermolecular Addition of Phenols and Carboxylic Acids to Olefins journal April 2005

Similar Records

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY