Colloidal Palladium Nanoparticles with In Situ H2: Reducing System for α,β-Unsaturated Carbonyl Compounds

Abstract A new reducing system comprising Pd(OAc)2 and NaBH4 in methanol to generate palladium nanoparticles has been efficiently utilized to reduce a variety of unsaturated carbonyl compounds. These were reduced to their corresponding saturated alcohols and fully saturated compounds in selected cases. This protocol presents alternative and mild reaction conditions for reduction.

[1]  O. Illa,et al.  Cyclopropanation of Cyclohexenone by Diazomethane Catalyzed by Palladium Diacetate: Evidence for the Formation of Palladium(0) Nanoparticles , 2007 .

[2]  W. Su,et al.  The palladium-catalyzed addition of aryl- and heteroarylboronic acids to aldehydes. , 2007, The Journal of organic chemistry.

[3]  Y. Monguchi,et al.  Chemoselective hydrogenation method catalyzed by Pd/C using diphenylsulfide as a reasonable catalyst poison , 2006 .

[4]  Kiran,et al.  Rapid reduction of chalcones to tetrahydrochalcones using nickel boride , 2006 .

[5]  H. Sajiki,et al.  Efficient C-H/C-D exchange reaction on the alkyl side chain of aromatic compounds using heterogeneous Pd/C in D2O. , 2004, Organic letters.

[6]  B. Ranu,et al.  Reduction of activated conjugated alkenes by the InCl3-NaBH4 reagent system , 2003 .

[7]  J. D. de Vries,et al.  Homeopathic ligand-free palladium as a catalyst in the heck reaction. A comparison with a palladacycle. , 2003, Organic letters.

[8]  C. Wai,et al.  Dispersing palladium nanoparticles using a water-in-oil microemulsion--homogenization of heterogeneous catalysis. , 2003, Chemical communications.

[9]  A. Biffis,et al.  Catalysis by metal nanoparticles supported on functional organic polymers , 2001 .

[10]  B. Ranu,et al.  Indium metal as a reducing agent. Selective reduction of the carbon-carbon double bond in highly activated conjugated alkenes. , 2001, Organic letters.

[11]  M. R. Pitts,et al.  Indium metal as a reducing agent in organic synthesis , 2001 .

[12]  J. Laumer,et al.  Controlled Release of Perfumery Aldehydes and Ketones by Norrish Type-II Photofragmentation of -Keto Esters in Undegassed Solution , 2000 .

[13]  A. Tagarelli,et al.  Mechanism and Extensibility of the Reaction , 2000 .

[14]  J. Jacquesy,et al.  Trapping of protonated phenols (ethers) by aromatics in superacids , 1998 .

[15]  J. Luche,et al.  Ultrasonically improved reductive properties of an aqueous ZnNiCl2 system-1 selective reduction of α,β-unsaturated carbonyl compounds , 1987 .

[16]  O. Arjona,et al.  Stereochemistry of addition to the carbonyl group. Part 17. Study of the factors affecting asymmetric induction in condensation reactions of methyl- and phenyl-magnesium bromide with chiral carbonyl compounds , 1981 .

[17]  B. Rickborn,et al.  Sodium borohydride reduction of conjugated aldehydes and ketones , 1970 .