{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,6]],"date-time":"2025-12-06T04:55:33Z","timestamp":1764996933900,"version":"build-2065373602"},"reference-count":118,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2012,2,1]],"date-time":"2012-02-01T00:00:00Z","timestamp":1328054400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2012,3,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Dichloro[bis{1\u2010(dicyclohexylphosphanyl)piperidine}]palladium [(P{(NC<jats:sub>5<\/jats:sub>H<jats:sub>10<\/jats:sub>)(C<jats:sub>6<\/jats:sub>H<jats:sub>11<\/jats:sub>)<jats:sub>2<\/jats:sub>})<jats:sub>2<\/jats:sub>PdCl<jats:sub>2<\/jats:sub>] (<jats:bold>1<\/jats:bold>) is a highly active and generally applicable C\uf8ffC cross\u2010coupling catalyst. Apart from its high catalytic activity in Suzuki, Heck, and Negishi reactions, compound <jats:bold>1<\/jats:bold> also efficiently converted various electronically activated, nonactivated, and deactivated aryl bromides, which may contain fluoride atoms, trifluoromethane groups, nitriles, acetals, ketones, aldehydes, ethers, esters, amides, as well as heterocyclic aryl bromides, such as pyridines and their derivatives, or thiophenes into their respective aromatic nitriles with K<jats:sub>4<\/jats:sub>[Fe(CN)<jats:sub>6<\/jats:sub>] as a cyanating agent within 24\u2005h in NMP at 140\u2009\u00b0C in the presence of only 0.05\u2005mol\u2009% catalyst. Catalyst\u2010deactivation processes showed that excess cyanide efficiently affected the molecular mechanisms as well as inhibited the catalysis when nanoparticles were involved, owing to the formation of inactive cyanide complexes, such as [Pd(CN)<jats:sub>4<\/jats:sub>]<jats:sup>2\u2212<\/jats:sup>, [(CN)<jats:sub>3<\/jats:sub>Pd(H)]<jats:sup>2\u2212<\/jats:sup>, and [(CN)<jats:sub>3<\/jats:sub>Pd(Ar)]<jats:sup>2\u2212<\/jats:sup>. Thus, the choice of cyanating agent is crucial for the success of the reaction because there is a sharp balance between the rate of cyanide production, efficient product formation, and catalyst poisoning. For example, whereas no product formation was obtained when cyanation reactions were examined with Zn(CN)<jats:sub>2<\/jats:sub> as the cyanating agent, aromatic nitriles were smoothly formed when hexacyanoferrate(II) was used instead. The reason for this striking difference in reactivity was due to the higher stability of hexacyanoferrate(II), which led to a lower rate of cyanide production, and hence, prevented catalyst\u2010deactivation processes. This pathway was confirmed by the colorimetric detection of cyanides: whereas the conversion of \u03b2\u2010solvato\u2010\u03b1\u2010cyanocobyrinic acid heptamethyl ester into dicyanocobyrinic acid heptamethyl ester indicated that the cyanide production of Zn(CN)<jats:sub>2<\/jats:sub> proceeded at 25\u2009\u00b0C in NMP, reaction temperatures of &gt;100\u2009\u00b0C were required for cyanide production with K<jats:sub>4<\/jats:sub>[Fe(CN)<jats:sub>6<\/jats:sub>]. Mechanistic investigations demonstrate that palladium nanoparticles were the catalytically active form of compound <jats:bold>1<\/jats:bold>.<\/jats:p>","DOI":"10.1002\/chem.201102936","type":"journal-article","created":{"date-parts":[[2012,2,1]],"date-time":"2012-02-01T12:24:06Z","timestamp":1328099046000},"page":"2978-2986","source":"Crossref","is-referenced-by-count":49,"title":["Cyanation of Aryl Bromides with K<sub>4<\/sub>[Fe(CN)<sub>6<\/sub>] Catalyzed by Dichloro[bis{1\u2010(dicyclohexylphosphanyl)piperidine}]palladium, a Molecular Source of Nanoparticles, and the Reactions Involved in the Catalyst\u2010Deactivation Processes"],"prefix":"10.1002","volume":"18","author":[{"given":"Roman","family":"Gerber","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miriam","family":"Oberholzer","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christian M.","family":"Frech","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,2]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"volume-title":"Houben\u2010Weyl: Methoden der organischen Chemie, Vol.\u2005E5","year":"1985","author":"Grundmann C.","key":"e_1_2_6_2_2"},{"volume-title":"Comprehensive Organic Transformations","year":"1989","author":"Larock R. C.","key":"e_1_2_6_3_2"},{"key":"e_1_2_6_4_2","first-page":"241","volume-title":"Pharmaceutical Substances: Syntheses, Patents, Applications","author":"Kleemann A.","year":"2001"},{"volume-title":"Chemistry of the Cyano Group","year":"1970","author":"Rappoport Z.","key":"e_1_2_6_5_2"},{"key":"e_1_2_6_6_2","unstructured":"6\u2010Aminopyridine\u20102\u2010carbonitriles for example are important synthetic intermediates in various pharmaceutically active compounds such as 6\u2010aminopyridine\u20102\u2010carboxamides which have applications as serotonin (5\u2010hydroxytryptamine) (5\u2010ht)\u2010receptor ligands (in particular for the 5\u2010ht6subtype).[5]Hence these nitriles are useful for the treatment of diseases for which modulation of the activity of the 5\u2010ht receptor is desired. Thus 6\u2010aminopyridine\u20102\u2010carboxamides could find their application in the enhancement of cognition and memory in patients with Alzheimer\u2019s disease [6]in the treatment of attention deficit hyperactivity disorder (ADHD) [7]and in the treatment of diseases of the central nervous system such as schizophrenia and depression.[8]In addition 5\u2010ht6\u2010receptor antagonists are useful in the treatment of obesity.[9]Another class of compound with pharmaceutical importance that involve 6\u2010aminopyridine\u20102\u2010carbonitriles as synthetic intermediates are 3\u2010substituted imidazo[1 5\u2212a]pyridin\u20105\u2010amines which are sodium\/proton exchange inhibitors that are useful antianginal and cardioprotective agents.[10 \u200911]"},{"key":"e_1_2_6_7_2","unstructured":"E. M.Collantes J. B.Schwarz U.\u2005S. Pat. Appl. Publ. (2009) US 20090197859."},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-8993(96)01224-3"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.bjp.0702445"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.bjp.0703288"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00213-003-1552-5"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1523\/JNEUROSCI.18-15-05901.1998"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.pharmtox.40.1.319"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2006.02.004"},{"key":"e_1_2_6_15_2","unstructured":"S.Ahmed S. C.Wu S. V.O\u2019Neil K.Ngu K. S.Atwal D. S.Weinstein U.\u2005S. Pat. Appl. Pub. (2000) US 7326705."},{"key":"e_1_2_6_16_2","unstructured":"Notably imidazo[1 5\u2212a]pyridines which have applications as organic light\u2010emitting diodes (OLEDs) and organic thin\u2010layer field\u2010effect transistors (FETs) are also prepared from pyridine\u20102\u2010carbonitriles. For example see:"},{"key":"e_1_2_6_17_2","unstructured":"D.Kitazawa G.Tominaga A.Takano Jpn. Kokai Tokkyo Koho JP 2001057292;"},{"key":"e_1_2_6_18_2","unstructured":"H. Nakamura and H.Yamamoto PCT Int. Appl. 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Ges."},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.188501801322"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.188401702202"},{"key":"e_1_2_6_29_2","unstructured":"\u00a0"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ie50477a013"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ie50485a019"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/B204244B"},{"key":"e_1_2_6_33_2","unstructured":"\u00a0"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0602571"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2004.10.045"},{"key":"e_1_2_6_36_2","first-page":"2683","author":"Veauthier J. 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The oxidative addition of an aryl halide onto the metal center of [Pd(L)n] (n=1 or 2) and subsequent transmetalation (with M\uf8ffCN) yield PdIIintermediates of type [Pd(Ar)(CN)(L)n] (and M\uf8ffX). Reductive elimination of Ar\uf8ffCN regenerates the catalyst.[19c\u2013e]"},{"key":"e_1_2_6_74_2","unstructured":"For examples where palladium nanoparticles have been proposed as the catalytically active form:"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.01.027"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1134\/S1070428010020016"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800295"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.05.124"},{"volume-title":"R\u00f6mpp Lexikon Chemie\u2014Version 2.0","year":"1999","key":"e_1_2_6_79_2"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903309"},{"key":"e_1_2_6_81_2","unstructured":"\u00a0"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201000942"},{"key":"e_1_2_6_83_2","unstructured":"M. Oberholzer R. Gerber C.\u2005M. Frech unpublished results;"},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201001201"},{"key":"e_1_2_6_85_2","unstructured":"Even though reaction temperatures of 120\u2009\u00b0C could be used for most of the substrates without a noticeable loss of activity the advantage of applying 140\u2009\u00b0C lay in the reliability and scope of the procedure which would allow the direct adoption of the procedure to other aryl bromides without the necessity of its modification."},{"key":"e_1_2_6_86_2","unstructured":"Cyanation reactions performed in protic solvents or with protic aryl halides (see below) are not appropriate because hydrolysis of CN\u2212into HCN could occur which competes with the aryl halide for oxidative addition onto the metal center. We assumed that the oxidative addition of HCN onto a bis\u2010phosphine palladium(0) metal center generates palladium\u2013hydride complexes of type [(PR3)2Pd(H)(CN)] which can react with another equivalent of HCN to give complexes of the type [(PR3)2Pd(CN)2] and H2.[27 \u200928]Subsequent phosphine substitution by cyanide generates [Pd(CN)4]2\u2212 which was indeed formed when the reactions were performed in protic solvents or protic aryl bromides."},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr950272y"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000247"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja078298h"},{"key":"e_1_2_6_90_2","unstructured":"\u00a0"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980762i"},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/om980897x"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja066931d"},{"key":"e_1_2_6_94_2","unstructured":"\u00a0"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic900053h"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac901977u"},{"key":"e_1_2_6_97_2","unstructured":"Another reason for the high catalytic performance of compound1with K4[Fe(CN)6] as the cyanating agent might be the reduction power of hexacyanoferrate(II) which could reduce (inactive)palladium(II)\u2013cyano complexes into catalytically active palladium(0) species. By analogy hexacyanoferrate(II) could also reduce traces of oxygen and other impurities from the reaction mixture."},{"key":"e_1_2_6_98_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.11.072"},{"key":"e_1_2_6_99_2","unstructured":"Notably even though full conversion of 1\u2010(6\u2010bromopyridin\u20102\u2010yl)\u20104\u2010methylpiperazine into 6\u2010(4\u2010methylpiperazin\u20101\u2010yl)pyridine\u20102\u2010carbonitrile was achieved within 24\u2005h no product formation was noted when 2\u2010bromo\u20106\u2010piperidin\u20101\u2010ylpyridine or 4\u2010(6\u2010bromopyridin\u20102\u2010yl)morpholine were used. The reason for the striking difference in reactivity of these structurally closely related compounds is unknown. Nevertheless because no product formation at all was observed when [Pd(OAc)2] or [Pd(OAc)2]\/dppf (dppf=1 1\u2032\u2010bis(diphenylphosphino)ferrocene) was used as the catalyst it cannot be excluded that trace amounts of an impurity is the reason for their unsuccessful cyanation."},{"key":"e_1_2_6_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp909019u"},{"key":"e_1_2_6_101_2","unstructured":"The morphologies of the nanoparticles also determine their catalytic activity. However nanoparticle morphology decisively depends on the conditions in which they are grown such as the concentration of palladium and the rate of catalyst degradation and hence on the rate of nanoparticle growth the presence of ligands and other additives as well as on the palladium source itself. This dependence explains the different catalytic activities of the pre\u2010catalysts. Moreover apart from the excellent catalytic activity of dichloro\u2010bis(1\u2010(dicyclohexylphosphanyl)piperidine)palladium (1) in the cyanation reaction aminophosphines have an additional advantage when compared to water\u2010insoluble phosphine\u2010based ligand systems: the treatment of compound1under work\u2010up conditions in air was recently shown to lead to rapid and complete catalyst degradation into decomposition products that were easily separated from the coupling products\u2014an often ignored but very important issue for the preparation of pharmaceutically active compounds etc."},{"key":"e_1_2_6_102_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(02)00728-8"},{"key":"e_1_2_6_103_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2004.05.015"},{"key":"e_1_2_6_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm0001556"},{"key":"e_1_2_6_105_2","unstructured":"\u00a0"},{"key":"e_1_2_6_106_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9705102"},{"key":"e_1_2_6_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja021436c"},{"key":"e_1_2_6_108_2","unstructured":"Tetrabutylammonium bromide is known to stabilize palladium nanoparticles. For example see:"},{"key":"e_1_2_6_109_2","first-page":"153","volume-title":"Advances in Metal\u2010Organic Chemistry, Vol. 5","author":"In T. 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