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Topics in Catalysis
Published in: Topics in Catalysis 14/2018

20-08-2018 | Original Paper

Pd(II)–Ni(II) Pyrazolate Framework as Active and Recyclable Catalyst for the Hydroamination of Terminal Alkynes

Authors: Francisco G. Cirujano, Elena López-Maya, J. A. R. Navarro, Dirk E. De Vos

Published in: Topics in Catalysis | Issue 14/2018

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Abstract

Well-dispersed [Pd(NH3)4]2+ sites have been introduced in the defective nickel pyrazolate porous framework, known as K@NiBDP. The resulting porous crystalline material shows a superior catalytic behavior for C–N bond formations than [Pd(NH3)4]2+ containing zeolite HY. The palladium exchanged catalyst, Pd@NiBDP, is able to promote both intra- and intermolecular hydroamination of terminal alkynes with excellent activity, reusability and selectivity towards the corresponding indole or imine versus the hydration of the alkyne. The same Pd species introduced in the microporous acid HY zeolite favors the hydration of the terminal alkyne towards the corresponding ketone, instead of the addition of the amine to the triple bond.

Graphical Abstract

previous article Variable-Temperature XAFS Analysis of SiO2-Supported Pd–Bisphosphine Complexes With/Without Co-immobilized Organic Functionality
next article Hierarchical Porosity Tailoring of Sol–Gel Derived Pt/SiO2 Catalysts

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Appendix
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Literature
1.
Taylor AP, Robinson RP, Fobian YM, Blakemore DC, Jones LH, Fadeyi O (2016) Modern advances in heterocyclic chemistry in drug discovery. Org Biomol Chem 14:6611–6637CrossRefPubMed
2.
Bechtoldt A, Tirler C, Raghuvanshi K, Warratz S, Kornhaaß C, Ackermann L (2016) Ruthenium oxidase catalysis for site-selective C–H alkenylations with ambient O2 as the sole oxidant. Angew Chem Int Ed 55:264–267CrossRef
3.
Ackermann L (2005) General and efficient indole syntheses based on catalytic amination reactions. Org Lett 7:439–442CrossRefPubMed
4.
Ackermann L, Barfüßer S, Potukuchi HK (2009) Copper-catalyzed N-arylation/hydroamination domino synthesis of indoles and its application to the preparation of a chek1/KDR kinase inhibitor pharmacophore. Adv Synth Catal 351:1064–1072CrossRef
5.
Ackermann L, Althammer A (2007) Domino N-H/C-H bond activation: palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes. Angew Chem Int Ed 46:1627–1629CrossRef
6.
Gates BC (2016) Concluding remarks: progress toward the design of solid catalysts. Faraday Discuss 188:591–602CrossRefPubMed
7.
Cirujano FG (2017) MOFs vs. zeolites: carbonyl activation with M(IV) catalytic sites. Catal Sci Technol 7:5482–5494CrossRef
8.
Santoro S, Kozhushkov SI, Ackermann L, Vaccaro L (2016) Heterogeneous catalytic approaches in C–H activation reactions. Green Chem 18:3471–3493CrossRef
9.
Alonso F, Beletskaya IP, Yus M (2005) Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Tetrahedron 61:11771–11835CrossRef
10.
Sachtler WMH, Cavalcanti FAP (1991) Coordination, atom reorganization, and catalysis of palladium in zeolite cages. Catal Lett 9:261–271CrossRef
11.
Sachtler WMH (1993) Metal clusters in zeolites: an intriguing class of catalysts. Acc Chem Res 26:383–387CrossRef
12.
13.
Djakovitch L, Dufaud V, Zaidi R (2006) Heterogeneous palladium catalysts applied to the synthesis of 2- and 2,3-functionalised indoles. Adv Synth Catal 348(6):715–724CrossRef
14.
Djakovitch L, Rouge P (2007) New homogeneously and heterogeneously [Pd/Cu]-catalysed C3-alkenylation of free NH-indoles. J Mol Catal A 273:230–239CrossRef
15.
Li H, Zhu Z, Zhang F, Xie S, Li H, Li P, Zhou X (2011) Palladium nanoparticles confined in the cages of MIL-101: an efficient catalyst for the one-pot indole synthesis in water. ACS Catal 1:1604–1612CrossRef
16.
Manna K, Zhang T, Lin W (2014) Postsynthetic metalation of bipyridyl-containing metal–organic frameworks for highly efficient catalytic organic transformations. J Am Chem Soc 136:6566–6569CrossRefPubMed
17.
Huang YB, Shen M, Wang X, Huang P, Chen R, Lin ZJ, Cao R (2016) Water-medium C–H activation over a hydrophobic perfluoroalkane-decorated metal-organic framework platform. J Catal 333:1–7CrossRef
18.
López-Maya E, Montoro C, Colombo V, Barea E, Navarro JAR (2014) Improved CO2 capture from flue gas by basic sites, charge gradients, and missing linker defects on nickel face cubic centered MOFs. Adv Funct Mater 24:6130–6135CrossRef
19.
Montoro C, Ocõn P, Zamora F, Navarro JAR (2016) Metal–organic frameworks containing missing-linker defects leading to high hydroxide-ion conductivity chem. Eur J 22:1646–1651CrossRef
20.
Rodríguez-Albelo LM, López-Maya E, Hamad S, Ruiz-Salvador R, Calero S, Navarro JAR (2017) Selective sulfur dioxide adsorption on crystal defect sites on an isoreticular metal organic framework series. Nat Commun 8:14457CrossRefPubMedPubMedCentral
21.
Cirujano FG, López-Maya E, Rodríguez-Albelo M, Barea E, Navarro JAR, De Vos DE (2017) Selective one-pot two-step C–C bond formation using metal–organic frameworks with mild basicity as heterogeneous catalysts. ChemCatChem 9:4019–4023CrossRef
22.
Djakovitch L, Koehler K (2001) Heck reaction catalyzed by Pd-modified zeolites. J Am Chem Soc 123:5990–5999CrossRefPubMed
23.
Noel S, Luo C, Pinel C, Djakovitch L (2007) efficient heterogeneously palladium-catalysed Heck arylation of acrolein diethyl acetal. Selective synthesis of cinnamaldehydes or 3-arylpropionic esters. Adv Synth Catal 349(7):1128–1140CrossRef
24.
Augustyniak AW, Zawartka W, Navarro JAR, Trzeciak AM (2016) Palladium nanoparticles supported on a nickel pyrazolate metal organic framework as a catalyst for Suzuki and carbonylative Suzuki couplings. Dalton Trans 45:13525–13531CrossRefPubMed
25.
Fortea-Pérez FR, Mon M, Ferrando-Soria J, Boronat M, Leyva-Pérez A, Corma A, Herrera JM, Osadchii D, Gascon J, Armentano D, Pardo E (2017) The MOF-driven synthesis of supported palladium clusters with catalytic activity for carbene-mediated chemistry. Nat Mater 16:760–766PubMed
26.
Mueller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Hydroamination: direct addition of amines to alkenes and alkynes. Chem Rev 108:3795–3892CrossRef
27.
Penzien J, Haeßner C, Jentys A, Köhler K, Müller TE, Lercher JA (2004) Heterogeneous catalysts for hydroamination reactions: structure–activity relationship. J Catal 221:302–312CrossRef
28.
Rubio-Marqués P, Rivero-Crespo MA, Leyva-Pérez A, Corma A (2015) Well-defined noble metal single sites in zeolites as an alternative to catalysis by insoluble metal salts. J Am Chem Soc 137:11832–11837CrossRefPubMed
29.
Marquez C, Rivera-Torrente M, Paalanen PP, Weckhuysen BM, Cirujano FG, De Vos D, De Baerdemaeker T (2017) Increasing the availability of active sites in Zn-Co double metal cyanides by dispersion onto a SiO2 support. J Catal 354:92–99CrossRef
30.
Perry CH, Athans DP, Young EF (1967) Far infrared spectra of palladium compounds. Spectrochim Acta 173:1137–1147CrossRef
31.
Cabrero-Antonino JR, Leyva-Pérez A, Corma A (2015) Beyond acid strength in zeolites: soft framework counteranions for stabilization of carbocations on zeolites and its implication in organic synthesis. Angew Chem Int Ed 54:5658–5661CrossRef
32.
33.
Liu W, Wang H, Li CJ (2016) Metal-free markovnikov-type alkyne hydration under mild conditions. Org Lett 18:2184–2187CrossRefPubMed
34.
La Sorella G, Sperni L, Ballester P, Strukula G, Scarso A (2016) Hydration of aromatic alkynes catalyzed by a self-assembled hexameric organic capsule. Catal Sci Technol 6:6031–6036CrossRef
35.
Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquerol J, Siemieniewska T (1985) Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity. Pure Appl Chem 57:603–619CrossRef
36.
Chen Q, Lv L, Yu M, Shi Y, Li Y, Pang G. Cao C (2013) Simple, efficient and reusable Pd–NHC catalysts for hydroamination. RSC Adv 3:18359–18366CrossRef
Metadata
Title
Pd(II)–Ni(II) Pyrazolate Framework as Active and Recyclable Catalyst for the Hydroamination of Terminal Alkynes
Authors
Francisco G. Cirujano
Elena López-Maya
J. A. R. Navarro
Dirk E. De Vos
Publication date
20-08-2018
Publisher
Springer US
Published in
Topics in Catalysis / Issue 14/2018
Print ISSN: 1022-5528
Electronic ISSN: 1572-9028
DOI
https://doi.org/10.1007/s11244-018-1039-6

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