Concerted Catalysis by Adjacent Palladium and Gold in Alloy Nanoparticles for the Versatile and Practical [2+2+2] Cycloaddition of Alkynes

Miura, Hideo; Tanaka, Yumi; Nakahara, Karin; Hachiya, Yuka; Endo, Kazuhiko; Shishido, Tetsuya

doi:10.1002/anie.201800973

Cited by 40 publications

(21 citation statements)

References 32 publications

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“…Supported Pd–Au alloy catalysts were prepared by a colloid immobilization method. , PVA and NaBH 4 aqueous solution were used as protecting and reducing agents, respectively. More detailed descriptions of the preparation methods are in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Highly Efficient Supported Palladium–Gold Alloy Catalysts for Hydrogen Storage Based on Ammonium Bicarbonate/Formate Redox Cycle

Nakajima

Tominaga

Waseda

et al. 2019

ACS Sustainable Chem. Eng.

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We have developed supported Pd–Au alloy catalysts for reversible hydrogen storage–release process with high efficiency based on the reversible reactions involving ammonium formate and bicarbonate. Supported Pd–Au random alloy catalysts exhibited a superior activity than supported monometallic Pd and Au catalysts in both bicarbonate hydrogenation and formate dehydrogenation under ambient conditions even without additives such as acids or bases. We used a series of Pd–Au alloy nanoparticles (NPs) supported on active carbon (Pd–Au/AC) with various Au/Pd ratios ranging from 0.1 to 10 to investigate the effects of the Au/Pd ratio. Turn over frequency (TOF) of bicarbonate hydrogenation increased monotonically with the Au/Pd ratio. Conversely, we found a volcano type relationship between the TOF of formate dehydrogenation and Au/Pd ratio and 1Au1Pd/AC catalyst exhibited the highest TOF value. On the basis of our structural and kinetic analysis, we discuss the correlation between the activity and the state of Pd and Au in supported Pd–Au alloy NPs.

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Section: Methodsmentioning

confidence: 99%

Highly Efficient Supported Palladium–Gold Alloy Catalysts for Hydrogen Storage Based on Ammonium Bicarbonate/Formate Redox Cycle

Nakajima

Tominaga

Waseda

et al. 2019

ACS Sustainable Chem. Eng.

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“…In 2018, Shishido, Miura, and co-workers reported the [2+2+2] cycloaddition reaction of substituted alkynes over supported Pd-Au alloy catalysts prepared through a sol-immobilization method (Scheme 51). 113 The Pd/Au ratio was a crucial factor for the catalytic activity and the compatibility of this catalyst with open-air conditions. Notably, the 1Pd4Au/TiO 2 catalyst was highly air tolerant and allowed the [2+2+2] cross-cycloaddition of 1,6-diynes with alkynes on a wide substrate scope in 37-95% yield.…”

Section: Other Metal-catalyzed [2+2+2] Cycloadditionmentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.1 Introduction2 Formation of Carbocycles2.1 Intermolecular Reactions2.1.1 Cyclotrimerization of Alkynes2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.1 Cycloaddition of Alkynes with Nitriles3.2 Cycloaddition of 1,6-Diynes with Cyanamides3.3 Cycloaddition of 1,6-Diynes with Selenocyanates3.4 Cycloaddition of Imines with Allenes or Alkenes3.5 Cycloaddition of (Thio)Cyanates and Isocyanates3.6 Cycloaddition of 1,3,5-Triazines with Allenes3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion

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“…As solid catalysts, synergistic effects ascribed to the concomitant presence of two metals within nanosized aggregates, nanoclusters or nanoparticles, have been shown to unlock favourable, in some instances unique, catalytic performances in a broad range of conversion processes. [7][8][9][10] Pioneering work in this area by Sinfelt et al in alkane dehydrogenation and hydrogenolysis reactions 11,12 was followed by a surge of studies which demonstrated the potential of bimetallic catalysts in a wide array of reactions, from oxidation, [13][14][15] to hydrogenation, [16][17][18][19][20] reforming, 21 biomass conversion, 5 C-C coupling, 22 or acetoxylation catalysis. 23 The distinctive catalytic properties of bimetallics compared to their monometallic counterparts has been associated to factors such as differences in lattice strain and surface topology, intermetallic charge transfer phenomena, or atomic-scale surface dilution phenomena of one metal within a matrix of second metal (also referred to as single-atom alloys).…”

Section: Introductionmentioning

confidence: 99%

Bottom-up assembly of bimetallic nanocluster catalysts from oxide-supported single-atom precursors

et al. 2021

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Concerted Catalysis by Adjacent Palladium and Gold in Alloy Nanoparticles for the Versatile and Practical [2+2+2] Cycloaddition of Alkynes

Cited by 40 publications

References 32 publications

Highly Efficient Supported Palladium–Gold Alloy Catalysts for Hydrogen Storage Based on Ammonium Bicarbonate/Formate Redox Cycle

Highly Efficient Supported Palladium–Gold Alloy Catalysts for Hydrogen Storage Based on Ammonium Bicarbonate/Formate Redox Cycle

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Bottom-up assembly of bimetallic nanocluster catalysts from oxide-supported single-atom precursors

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