Диссертация (1150164), страница 21
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С увеличением активности вряду:монопротонный(2aDBA@PS),дипротонный(2aBHA@PS),наблюдаетсяуменьшение стабильности ADC-PdII комплексов к действию Et3N и увеличение долипереходящих в раствор каталитических форм.115Работавыполненагосударственногоприфинансовойуниверситета(грантподдержке№Санкт-Петербургского12.38.195.2014),Министерстваобразования и науки РФ (грант № МК-3322.2014.3) и РФФИ (грант №14-03-32015), атакже с использованием оборудования ресурсных центров СПбГУ («Магнитнорезонансные методы исследования», «Методы анализа состава вещества»,«Рентгенодифракционныеметодыисследования»,«Физическиеметодыисследования поверхности», «Термогравиметрические и калориметрические методыисследования» и «Образовательного ресурсного центра по направлению химия»).Автор выражает благодарность сотрудникам РЦ за помощь при выполненииработы.116[1]Список литературы:Recent Progress in the Use of Pd-Catalyzed C–C Cross-Coupling Reactions in theSynthesis of Pharmaceutical Compounds / A.
F. P. Biajoli, C. S. Schwalm, J. Limbergeret al. // J. Braz. Chem. Soc. - 2014. – Vol. 25, No. 12. – P. 2186–2214.[2]Torborg C. Recent Applications of Palladium–Catalyzed Coupling Reactions in thePharmaceutical, Agrochemical, and Fine Chemical Industries / C. Torborg, M. Beller //Adv. Synth. Catal. – 2009. – Vol. 351, No. 18. – P.
3027–3043.[3]Colacot T. Commercial Development of Palladium(0) Catalysts for Highly SelectiveCross–Coupling Reactions / T. Colacot // Platin. Met. Rev. – 2012. – Vol. 56, No. 2. – P.110–116.[4]Boeda F. N–Heterocyclic carbene–containing complexes in catalysis / F. Boeda, S. P.Nolan // Annu. Reports Sect. ―B‖ Organic Chem. – 2008.
– Vol. 104. – P. 184–210.[5]Fortman G. C. N–Heterocyclic carbene (NHC) ligands and palladium in homogeneouscross–coupling catalysis: a perfect union / G. C. Fortman, S. P. Nolan // Chem. Soc. Rev.– 2011. – Vol. 40, No. 10. – P. 5151–5169.[6]Hoyos M. ( N –Heterocyclic Carbene)–Palladium Complexes in Catalysis / M. Hoyos,D. Guest, O. Navarro // in N–Heterocyclic Carbenes – 2014. – Vol. 4, Weinheim,Germany: Wiley–VCH Verlag GmbH & Co. KGaA, 2014. – P. 85–110.[7]Recent progress of N–heterocyclic carbenes in heterogeneous catalysis / K.
V. S.Ranganath, S. Onitsuka, A. K. Kumar, and J. Inanaga // Catal. Sci. Technol. – 2013. –Vol. 3, No. 9. – P. 2161–2181.[8]Sommer W. J. Supported N–heterocyclic carbene complexes in catalysis / W. J. Sommer,M. Weck // Coord. Chem. Rev. – 2007. – Vol. 251, No. 5–6. – P. 860–873.[9]Slaughter L. M. ―Covalent Self–Assembly‖ Of Acyclic Diaminocarbene Ligands AtMetal Centers / L. M. Slaughter // Comments Inorg. Chem. – 2008. – Vol. 29, No. 1–2. –P.
46–72.[10] Slaughter L. M. Acyclic Aminocarbenes in Catalysis / L. M. Slaughter // ACS Catal. –2012. – Vol. 2, No. 8. – P. 1802–1816.[11] Boyarskiy V. P. Acyclic diaminocarbenes (ADCs) as a promising alternative to N–heterocyclic carbenes (NHCs) in transition metal catalyzed organic transformations / V.P.
Boyarskiy, K. V. Luzyanin, and V. Y. Kukushkin // Coord. Chem. Rev. – 2012. –Vol. 256, No. 17–18. – P. 2029–2056.117[12] Slaughter L. M. Catalysis with Acyclic Aminocarbene Ligands: Alternatives to NHCswith Distinct Steric and Electronic Properties / L. M. Slaughter // in N–HeterocyclicCarbenes – 2014, Weinheim, Germany: Wiley–VCH Verlag GmbH & Co. KGaA, 2014.– P.
499–524.[13] Boyarskiy V. P. Palladium–(Acyclic Diaminocarbene) Species as Alternative toPalladium–(Nitrogen Heterocyclic Carbenes) in Cross–Coupling Catalysis / V. P.Boyarskiy, K. V. Luzyanin, and V. Y. Kukushkin // in Advances in OrganometallicChemistry and Catalysis – 2013. – Vol. 53, No. 9, Hoboken, NJ, USA: John Wiley &Sons, Inc., 2013. – P. 145–155.[14] Merrifield resin supported Pd–NHC complex with a spacer(Pd–NHC@SP–PS) for theSonogashira coupling reaction under copper– and solvent–free conditions / S. N.
Jadhav,A. S. Kumbhar, S. S. Mali et al. // New J. Chem. – 2015. – Vol. 39, No. 3. – P. 2333–2341.[15] Mohammadi E. Synthesis of polystyrene–supported Pd(II)–NHC complex derived fromtheophylline as an efficient and reusable heterogeneous catalyst for the Heck–Matsudacross–coupling reaction / E. Mohammadi, B. Movassagh // J. Mol. Catal. A Chem. –2016. – Vol. 418–419. – P. 158–167.[16] Polymer–supported Pd–NHC complexes: Strategies for the development ofmultifunctional systems / V.
Sans, F. Gelat, M. I. Burguete et al. // Catal. Today – 2012.– Vol. 196, No. 1. – P. 137–147.[17] The use of NIR–FT–Raman spectroscopy for the characterization of polymer–supportedreagents and catalysts / B. Altava, M. Burguete, E. Garc a–Verdugo et al. // Tetrahedron– 2001.
– Vol. 57, No. 41. – P. 8675–8683.[18] A sensitive colorimetric method for the study of polystyrene merrifield resins andchloromethylated macroporous monolithic polymers / F. Galindo, B. Altava, M. I.Burguete et al. // J. Comb. Chem. – 2004. – Vol. 6, No. 6. – P. 859–861.[19] A viable synthesis of ferrocene tethered NHC–Pd complex via supported ionic liquidphase catalyst and its Suzuki coupling activity / V. Gaikwad, R. Kurane, J.
Jadhav, R.Salunkhe et al. // Appl. Catal. A Gen. – 2013. – Vol. 451. – P. 243–250.[20] Pd catalysts immobilized onto gel–supported ionic liquid–like phases (g–SILLPs): Aremarkable effect of the nature of the support / M. I. Burguete, E.
García–Verdugo, I.Garcia–Villar et al. // J. Catal. – 2010. – Vol. 269, No. 1. – P. 150–160.118[21] Symmetrical bis–(NHC) palladium(II) complexes: Synthesis, structure, and applicationin catalysis / N. B. Jokić, C. S. Straubinger, S. Li Min Goh et al. // Inorganica Chim.Acta – 2010. – Vol. 363, No. 15. – P. 4181–4188.[22] Tuning the Catalytic Efficiency of Palladium Supported Complexes (Pd–NHC–SILLPs):The Cooperative Effect of the Ionic Liquid–Like Groups / V. Sans, F. Gelat, M. I.Burguete et al.
// Macromol. Symp. – 2012. – Vol. 317–318, No. 1. – P. 259–266.[23] A magnetically separable palladium catalyst containing a bulky N–heterocyclic carbeneligand for the Suzuki–Miyaura reaction / Z. Wang, Y. Yu, Y. X. Zhang et al. // GreenChem. – 2015. – Vol. 17, No. 1. – P. 413–420.[24] Polymer supported ionic liquid phases (SILPs) versus ionic liquids (ILs): how much dothey look alike / M. I. Burguete, F.
Galindo, E. García–Verdugo et al. // Chem.Commun. (Camb). – 2007, No. 29. – P. 3086–8.[25] Forns P. Merrifield Resin / P. Forns, F. Albericio // in Encyclopedia of Reagents forOrganic Synthesis – 2003, Chichester, UK: John Wiley & Sons, Ltd, 2003. – P. 1–7.[26] Byun J.–W. Preparation of polymer–supported palladium/N–heterocyclic carbenecomplex for Suzuki cross–coupling reactions / J.–W. Byun, Y.–S. Lee // TetrahedronLett. – 2004. – Vol. 45, No. 9.
– P. 1837–1840.[27] Nan G. Suzuki–Miyaura cross–coupling reaction of 1–aryltriazenes with arylboronicacids catalyzed by a recyclable polymer–supported N–heterocyclic carbene–palladiumcomplex catalyst / G. Nan, F. Ren, M. Luo // Beilstein J. Org. Chem. – 2010. – Vol. 6,No. 70. – P.
1–6.[28] Polymer–Supported Ionic–Liquid–Like Phases (SILLPs): Transferring Ionic LiquidProperties to Polymeric Matrices / V. Sans, N. Karbass, M. I. Burguete et al. // Chem. –A Eur. J. – 2011. – Vol. 17, No. 6. – P. 1894–1906.[29] Lo H. K. Synthesis of PS–supported NHC–Pd catalyst derived from theobromine and itsapplications in Suzuki–Miyaura reaction / H. K. Lo, F. T. Luo // J. Chinese Chem. Soc. –2012. – Vol. 59, No. 3.
– P. 394–398.[30] Kim J.–H. Polymer–supported N–heterocyclic carbene–palladium complex forheterogeneous Suzuki cross–coupling reaction / J.–H. Kim, J.–W. Kim, M.Shokouhimehr, Y.–S. Lee // J. Org. Chem. – 2005. – Vol. 70, No. 17. – P. 6714–20.[31] Toward Tunable Immobilized Molecular Catalysts: Functionalizing the MethyleneBridge of Bis(N–heterocyclic carbene) Ligands / R. Zhong, A. Pöthig, S.
Haslinger et al.119// Chempluschem – 2014. – Vol. 79, No. 9. – P. 1294–1303.[32] Khairnar B. Amidation of Aryl Halides with Isocyanides Using a Polymer–SupportedPalladium–N–Heterocyclic Carbene Complex as an Efficient, Phosphine–Free andHeterogeneous Recyclable Catalyst / B. Khairnar, B. Bhanage // Synthesis (Stuttg). –2014. – Vol. 46, No. 09. – P. 1236–1242.[33] Carbonylative Cyclization of o–Halobenzoic Acids for Synthesis of N–SubstitutedPhthalimides Using Polymer–Supported Palladium–N–Heterocyclic Carbene as anEfficient, Heterogeneous, and Reusable Catalyst / M. Khedkar, S.
Khan, K. Dhake, B.Bhanage // Synthesis (Stuttg). – 2012. – Vol. 44, No. 16. – P. 2623–2629.[34] A Simple, Efficient, and Recyclable Phosphine–Free Catalytic System for CarbonylativeSuzuki Coupling Reaction of Aryl and Heteroaryl Iodides / Z. Qureshi, K. Deshmukh, P.Tambade, B. Bhanage // Synthesis (Stuttg). – 2011. – Vol.
2011, No. 02. – P. 243–250.[35] An efficient and heterogeneous recyclable palladium catalyst for chemoselectiveconjugate reduction of α,β–unsaturated carbonyls in aqueous medium / D. B. Bagal, Z.S. Qureshi, K. P. Dhake et al. // Green Chem. – 2011. – Vol. 13, No. 6. – P.
1490–1494.[36] PS–Pd–NHC: an efficient and heterogeneous recyclable catalyst for direct reductiveamination of carbonyl compounds with primary/secondary amines in aqueous medium /D. B. Bagal, R. A. Watile, M. V. Khedkar et al. // Catal. Sci. Technol. – 2012. – Vol. 2,No. 2. – P. 354–358.[37] Aminocarbonylation of aryl iodides with primary and secondary amines in aqueousmedium using polymer supported palladium–N–heterocyclic carbene complex as anefficient and heterogeneous recyclable catalyst / Z.
S. Qureshi, S. A. Revankar, M. V.Khedkar, B. M. Bhanage // Catal. Today – 2012. – Vol. 198, No. 1. – P. 148–153.[38] Polymer–supported Pd–NHC complexes: Strategies for the development ofmultifunctional systems / V. Sans, F. Gelat, M. I. Burguete et al. // Catal. Today – 2012.– Vol. 196, No. 1. – P. 137–147.[39] N–Heterocyclic carbene–palladium complex on polystyrene resin surface as polymer–supported catalyst and its application in Suzuki cross–coupling reaction / J.–H.