Supported Palladium Nanoparticle Catalyzed α-Alkylation of Ketones Using Alcohols as Alkylating Agents

Polymer stabilized palladium (Pd@PS) nanoparticles (NPs) catalyzed α-alkylation of acyclic, cyclic, and aliphatic ketones were performed with methanol, ethanol, and long chain alkyl and benzyl alcohols. The heterogeneous catalyst, Pd@PS, was found to be highly active for most challenging small chain alkyl alcohols such as methanol and ethanol in alkylation reaction following oxidation, condensation, and reduction approaches.

[1]  P. Das,et al.  Supported palladium nanoparticles as switchable catalyst for aldehyde conjugate/s and acetate ester syntheses from alcohols , 2017 .

[2]  A. Seayad,et al.  A Convenient Ruthenium‐Catalysed α‐Methylation of Carbonyl Compounds using Methanol , 2016 .

[3]  C. Su,et al.  N-Alkylation by Hydrogen Autotransfer Reactions , 2016, Topics in Current Chemistry.

[4]  P. Das,et al.  Oxidative “reverse-esterification” of ethanol with benzyl/alkyl alcohols or aldehydes catalyzed by supported rhodium nanoparticles , 2016 .

[5]  Neil G. Stevenson,et al.  Strategic Application and Transformation of ortho-Disubstituted Phenyl and Cyclopropyl Ketones To Expand the Scope of Hydrogen Borrowing Catalysis. , 2015, Journal of the American Chemical Society.

[6]  P. Das,et al.  Supported Palladium Nanoparticle-Catalyzed Carboxylation of Aryl Halides, Alkenylsilanes, and Organoboronic Acids Employing Oxalic Acid as the C1 Source. , 2015, Organic letters.

[7]  A. Seayad,et al.  An efficient heterogenized palladium catalyst for N-alkylation of amines and α-alkylation of ketones using alcohols , 2015 .

[8]  P. Das,et al.  Polystyrene trimethyl ammonium chloride impregnated Rh(0) (Rh@PMe3NCl) as a catalyst and methylating agent for esterification of alcohols through selective oxidation of methanol , 2015 .

[9]  P. Andersson,et al.  C-C coupling of ketones with methanol catalyzed by a N-heterocyclic carbene-phosphine iridium complex. , 2015, Chemistry.

[10]  Darren L. Poole,et al.  Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium** , 2014, Angewandte Chemie.

[11]  Feng Li,et al.  α-Alkylation of ketones with primary alcohols catalyzed by a Cp*Ir complex bearing a functional bipyridonate ligand. , 2014, The Journal of organic chemistry.

[12]  Y. Obora Recent Advances in α-Alkylation Reactions using Alcohols with Hydrogen Borrowing Methodologies , 2014 .

[13]  Xicheng Wang,et al.  Direct α-alkylation of ketones with alcohols in water. , 2014, ChemSusChem.

[14]  S. H. Siddiki,et al.  Self-Coupling of Secondary Alcohols and α-Alkylation of Methyl Ketones with Secondary Alcohols by Pt/CeO2 Catalyst , 2014, Topics in Catalysis.

[15]  Y. Obora,et al.  Iridium-catalyzed selective α-methylation of ketones with methanol. , 2014, Chemical communications.

[16]  Jianliang Xiao,et al.  DMF as carbon source: Rh-catalyzed α-methylation of ketones. , 2014, Organic letters.

[17]  Darren L. Poole,et al.  Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products** , 2013, Angewandte Chemie.

[18]  P. Das,et al.  Solid supported platinum(0) nanoparticles catalyzed chemo-selective reduction of nitroarenes to N-arylhydroxylamines , 2013 .

[19]  A. Tlili,et al.  More sustainable formation of C-N and C-C bonds for the synthesis of N-heterocycles. , 2013, Angewandte Chemie.

[20]  D. Milstein,et al.  Applications of Acceptorless Dehydrogenation and Related Transformations in Chemical Synthesis , 2013, Science.

[21]  R. Rodríguez‐Lugo,et al.  A homogeneous transition metal complex for clean hydrogen production from methanol-water mixtures. , 2013, Nature chemistry.

[22]  F. Glorius,et al.  N-formylation of amines by methanol activation. , 2013, Organic letters.

[23]  M. Beller,et al.  Low-temperature aqueous-phase methanol dehydrogenation to hydrogen and carbon dioxide , 2013, Nature.

[24]  D. Shah,et al.  Clean borrowing hydrogen methodology using hydrotalcite supported copper catalyst , 2013 .

[25]  P. Das,et al.  Solid‐Supported Rhodium(0) Nano‐/Microparticles: An Efficient Ligand‐Free Heterogeneous Catalyst for Microwave‐Assisted Suzuki–Miyaura Cross‐Coupling Reaction , 2012 .

[26]  T. Fukuyama,et al.  RuHCl(CO)(PPh3)3-catalyzed α-alkylation of ketones with primary alcohols. , 2012, Organic letters.

[27]  V. Sridharan,et al.  Iridium catalysed chemoselective alkylation of 2'-aminoacetophenone with primary benzyl type alcohols under microwave conditions. , 2012, Chemical communications.

[28]  Xiaochun Yu,et al.  Copper-catalyzed C-alkylation of secondary alcohols and methyl ketones with alcohols employing the aerobic relay race methodology. , 2012, Organic & biomolecular chemistry.

[29]  Qing Sun,et al.  Copper-catalyzed N-alkylation of amides and amines with alcohols employing the aerobic relay race methodology. , 2012, Organic & biomolecular chemistry.

[30]  Qing Sun,et al.  Discovery and mechanistic studies of a general air-promoted metal-catalyzed aerobic N-alkylation reaction of amides and amines with alcohols. , 2011, The Journal of organic chemistry.

[31]  P. Das,et al.  Solid-supported palladium nano and microparticles: an efficient heterogeneous catalyst for ligand-free Suzuki–Miyaura cross coupling reaction☆ , 2011 .

[32]  Ryan A. Mesch,et al.  Iridium-catalysed direct C–C coupling of methanol and allenes , 2011, Nature Chemistry.

[33]  Youquan Deng,et al.  Organic ligand-free alkylation of amines, carboxamides, sulfonamides, and ketones by using alcohols catalyzed by heterogeneous Ag/Mo oxides. , 2011, Chemistry.

[34]  M. Yus,et al.  Alcohols for the α‐Alkylation of Methyl Ketones and Indirect Aza‐Wittig Reaction Promoted by Nickel Nanoparticles , 2008 .

[35]  M. Yus,et al.  Alcohols as electrophiles in C--C bond-forming reactions: the hydrogen autotransfer process. , 2007, Angewandte Chemie.

[36]  R. Grigg,et al.  Sequential one-pot bimetallic Ir(III)/Pd(0) catalysed mono-/bis-alkylation and spirocyclisation processes of 1,3-dimethylbarbituric acid and allenes. , 2006, Chemical communications.

[37]  M. Yus,et al.  Easy α-alkylation of ketones with alcohols through a hydrogen autotransfer process catalyzed by RuCl2(DMSO)4 , 2006 .

[38]  Yoichi M. A. Yamada,et al.  A solid-phase self-organized catalyst of nanopalladium with main-chain viologen polymers: alpha-alkylation of ketones with primary alcohols. , 2006, Organic letters.

[39]  Seong Hyeok Seo,et al.  Recyclable Palladium Catalyst for Highly Selective α Alkylation of Ketones with Alcohols , 2005 .

[40]  C. Cho A palladium-catalyzed route for α-alkylation of ketones by primary alcohols , 2005 .

[41]  M. Yus,et al.  [Ru(DMSO)4]Cl2 catalyzes the α-alkylation of ketones by alcohols , 2005 .

[42]  S. Sakaguchi,et al.  An efficient direct alpha-alkylation of ketones with primary alcohols catalyzed by [Ir(cod)Cl]2/PPh3/KOH system without solvent. , 2004, Journal of the American Chemical Society.

[43]  C. Cho,et al.  Ruthenium-catalyzed regioselective a-alkylation of ketones with primary alcohols , 2002 .

[44]  J. Otera,et al.  Modern Carbonyl Chemistry , 2000 .

[45]  R. Grigg,et al.  Oxidation of ethanol by cobalt, iron, and rhodium complexes , 1977 .

[46]  Y. Obora,et al.  Conferences and Meetings , 1966, British medical journal.