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Kinetics and mechanisms of homogeneous catalytic reactions: Part 13. Regioselective reduction of quinoline catalysed by Rh(acac)(CO)[P(tBu)(CH2CH=CH2)
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  • 作者:Merlin Rosales ; Karely Molina ; Regina Vallejo…
  • 刊名:Transition Metal Chemistry
  • 出版年:2016
  • 出版时间:May 2016
  • 年:2016
  • 卷:41
  • 期:4
  • 页码:467-473
  • 全文大小:711 KB
  • 参考文献:1.Topsoe H, Clausen BS, Massoth FE (1996) Hydrotreating catalysis. Springer, BerlinCrossRef
    2.Bianchini C, Meli A, Vizza F (2001) Eur J Inorg Chem 43
    3.Sánchez-Delgado A (2000) In: James BR, van Leeuwen PWNM (eds) Organometallics modeling of the hydrodesulfurisation and hydrodenitrogenation reactions. Kluwer, Dordrecht, pp 84–92
    4.Fish RH, Michaels JN, Moore RS, Heinemann H (1990) J Catal 123:74CrossRef
    5.Fish RH, Tan JL, Thormodsen AD (1984) J Org Chem 49:4500CrossRef
    6.Fish RH, Kim HS, Babin JE, Adams RD (1988) Organometallics 7:2250CrossRef
    7.Baralt E, Smith SJ, Hurwitz J, Horváth IT, Fish RH (1992) J Am Chem Soc 114:5187CrossRef
    8.Sánchez-Delgado RA, González E (1989) Polyhedron 8:1431CrossRef
    9.Sánchez-Delgado RA, Rondón D, Andriollo A, Herrera V, Martín G, Chaudret B (1993) Organometallics 12:4291CrossRef
    10.Chin CS, Park Y, Lee B (1995) Catal Lett 31:239CrossRef
    11.Rosales M, Alvarado Y, Boves M, Rubio R, Sánchez-Delgado R, Soscún H (1995) Transit Met Chem 20:246
    12.Rosales M, Navarro J, Sánchez L, González A, Alvarado Y, Rubio R, De La Cruz C, Rajmankina T (1996) Transit Met Chem 21:11CrossRef
    13.Rosales M, González A, Navarro J, Soscún H, Zárraga J (1997) Inorg Chim Acta 257:131CrossRef
    14.Rosales M, Boves M, Soscún H, Ruette F (1998) J Mol Struct (Theochem) 433:319CrossRef
    15.Rosales M, Arrieta F, Castillo J, González A, Navarro J, Vallejo R (2000) Stud Surf Sci Catal 130D:3357CrossRef
    16.Rosales M, Castillo J, González A, González L, Molina K, Navarro J, Pacheco I, Pérez H (2004) Transit Met Chem 29:225
    17.Rosales M, Arteaga MA, González Á, González B, Molina K, Pérez H, Vallejo R (2006) Ciencia 14:70
    18.Rosales M, Alvarado B, Arrieta F, De La Cruz C, González A, Molina K, Soto O, Salazar Y (2008) Polyhedron 37:530CrossRef
    19.Alvarado Y, Busolo M, López-Linares F (1999) J Mol Catal 142:163CrossRef
    20.Rosales M, Chacón G, González A, Soto JJ, Vallejo R (2006) Catal Lett 106:101CrossRef
    21.Rosales M, Vallejo R, Bastidas LJ, González B, González A (2007) React Kin Catal Lett 92:99CrossRef
    22.Rosales M, Vallejo R, Soto JJ, Bastidas LJ, Molina K, Baricelli P (2010) Catal Lett 134:56CrossRef
    23.Rosales M, Bastidas LJ, Gonzalez B, Vallejo R, Baricelli P (2011) Catal Lett 141:1305CrossRef
    24.Borowski AF, Sabo-Etienne S, Donnadieu B, Chaudret B (2003) Organometallics 22:1630CrossRef
    25.PJ Dyson (2003) Dalton Trans 2964
    26.Pruchnik FP, Smolenski P, Wajda-Hermanowicz K (1998) J Organomet Chem 570:63CrossRef
    27.Braunstein P, Naud F, Dedieu A, Rohmer M-M, DeCian A, Rettig S (2001) Organometallics 20:2966CrossRef
    28.Jones NG, Green MLH, Vei I, Cowley A, Morize X, Braunstein P (2002) J Chem Soc Dalton Trans 1487
    29.Appleby T, Woollins JD (2002) Coord Chem Rev 235:121CrossRef
    30.Ocando-Mavarez E, Rosales M, Silva N (1998) Heteroatom Chem 9:253CrossRef
    31.Ocando-Mavarez E, Ascanio J, González T, Atencio R, Rosales M, Silva N (2003) Acta Cryst E59:m633
    32.Garcia JM, Coll DS, Ocando-Mavarez E, Ascanio J, Pekerar S, Atencio R, González T, Briceño A, Avila E, Rosales M (2014) Inorg Chim Acta 414:250CrossRef
    33.Casado J, López-Quintela MA, Lorenzo-Barral FM (1986) J Chem Ed 63:450CrossRef
    34.Brunner E (1985) J Chem Eng Data 30:269CrossRef
    35.Young CL (ed) (1981) Solubility data series, vol 5/6. Pergamon, Oxford, pp 176–420
    36.Crabtree RH, Anton DR (1983) Organometallics 2:855CrossRef
    37.Allen K, Bruck M, Gray S, Kingsborough R, Smith D, Weller K, Wigley D (1995) Polyhedron 14:3315CrossRef
  • 作者单位:Merlin Rosales (1)
    Karely Molina (1)
    Regina Vallejo (1)
    Edgar Ocando-Mavárez (2)

    1. Laboratorio de Química Inorgánica, Departamento de Química, Facultad Experimental de Ciencias, Universidad del Zulia (L.U.Z.), Apdo. 526, Maracaibo, Venezuela
    2. Centro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apdo. 21827, Caracas, 1020, Venezuela
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Catalysis
    Physical Chemistry
    Inorganic Chemistry
  • 出版者:Springer Netherlands
  • ISSN:1572-901X
文摘
The complex Rh(acac)(CO)[P(tBu)(CH2CH=CH2)2] (1) proved to be an efficient precatalyst for the regioselective hydrogenation of quinoline (Q) to 1,2,3,4-tetrahydroquinoline (THQ) under mild reaction conditions (125 °C and 4 atm H2). A kinetic study of this reaction led to the rate law: $$ r \, = \{ K_{1} k_{2} /(1 \, + \, K_{1} {\text{H}}_{ 2} )\} [{\text{Rh}}][{\text{H}}_{ 2} ]^{2} $$which becomes $$ r \, = \, K_{1} k_{2} [{\text{Rh}}][{\text{H}}_{ 2} ]^{2} $$at hydrogen pressures below 4 atm. The active catalytic species is the cationic complex {Rh(Q)2(CO)[P(tBu)(CH2CH=CH2)2]}+ (2). The mechanism involves the partial hydrogenation of one coordinated Q of (2) to yield a complex containing a 1,2-dihydroquinoline (DHQ) ligand, {Rh(DHQ)(Q)(CO)[P(tBu)(CH2CH=CH2)2]}+ (3), followed by hydrogenation of the DHQ ligand to give THQ and a coordinatively unsaturated species {Rh(Q)(CO)[P(tBu)(CH2CH=CH2)2]}+ (4); this reaction is considered to be the rate-determining step. Coordination of a new Q molecule to (4) regenerates the active species (2) and restarts the catalytic cycle. Page %P Close Plain text Look Inside Reference tools Export citation EndNote (.ENW) JabRef (.BIB) Mendeley (.BIB) Papers (.RIS) Zotero (.RIS) BibTeX (.BIB) Add to Papers Other actions Register for Journal Updates About This Journal Reprints and Permissions Share Share this content on Facebook Share this content on Twitter Share this content on LinkedIn Related Content Supplementary Material (0) References (37) References1.Topsoe H, Clausen BS, Massoth FE (1996) Hydrotreating catalysis. Springer, BerlinCrossRef2.Bianchini C, Meli A, Vizza F (2001) Eur J Inorg Chem 433.Sánchez-Delgado A (2000) In: James BR, van Leeuwen PWNM (eds) Organometallics modeling of the hydrodesulfurisation and hydrodenitrogenation reactions. Kluwer, Dordrecht, pp 84–924.Fish RH, Michaels JN, Moore RS, Heinemann H (1990) J Catal 123:74CrossRef5.Fish RH, Tan JL, Thormodsen AD (1984) J Org Chem 49:4500CrossRef6.Fish RH, Kim HS, Babin JE, Adams RD (1988) Organometallics 7:2250CrossRef7.Baralt E, Smith SJ, Hurwitz J, Horváth IT, Fish RH (1992) J Am Chem Soc 114:5187CrossRef8.Sánchez-Delgado RA, González E (1989) Polyhedron 8:1431CrossRef9.Sánchez-Delgado RA, Rondón D, Andriollo A, Herrera V, Martín G, Chaudret B (1993) Organometallics 12:4291CrossRef10.Chin CS, Park Y, Lee B (1995) Catal Lett 31:239CrossRef11.Rosales M, Alvarado Y, Boves M, Rubio R, Sánchez-Delgado R, Soscún H (1995) Transit Met Chem 20:24612.Rosales M, Navarro J, Sánchez L, González A, Alvarado Y, Rubio R, De La Cruz C, Rajmankina T (1996) Transit Met Chem 21:11CrossRef13.Rosales M, González A, Navarro J, Soscún H, Zárraga J (1997) Inorg Chim Acta 257:131CrossRef14.Rosales M, Boves M, Soscún H, Ruette F (1998) J Mol Struct (Theochem) 433:319CrossRef15.Rosales M, Arrieta F, Castillo J, González A, Navarro J, Vallejo R (2000) Stud Surf Sci Catal 130D:3357CrossRef16.Rosales M, Castillo J, González A, González L, Molina K, Navarro J, Pacheco I, Pérez H (2004) Transit Met Chem 29:22517.Rosales M, Arteaga MA, González Á, González B, Molina K, Pérez H, Vallejo R (2006) Ciencia 14:7018.Rosales M, Alvarado B, Arrieta F, De La Cruz C, González A, Molina K, Soto O, Salazar Y (2008) Polyhedron 37:530CrossRef19.Alvarado Y, Busolo M, López-Linares F (1999) J Mol Catal 142:163CrossRef20.Rosales M, Chacón G, González A, Soto JJ, Vallejo R (2006) Catal Lett 106:101CrossRef21.Rosales M, Vallejo R, Bastidas LJ, González B, González A (2007) React Kin Catal Lett 92:99CrossRef22.Rosales M, Vallejo R, Soto JJ, Bastidas LJ, Molina K, Baricelli P (2010) Catal Lett 134:56CrossRef23.Rosales M, Bastidas LJ, Gonzalez B, Vallejo R, Baricelli P (2011) Catal Lett 141:1305CrossRef24.Borowski AF, Sabo-Etienne S, Donnadieu B, Chaudret B (2003) Organometallics 22:1630CrossRef25.PJ Dyson (2003) Dalton Trans 296426.Pruchnik FP, Smolenski P, Wajda-Hermanowicz K (1998) J Organomet Chem 570:63CrossRef27.Braunstein P, Naud F, Dedieu A, Rohmer M-M, DeCian A, Rettig S (2001) Organometallics 20:2966CrossRef28.Jones NG, Green MLH, Vei I, Cowley A, Morize X, Braunstein P (2002) J Chem Soc Dalton Trans 148729.Appleby T, Woollins JD (2002) Coord Chem Rev 235:121CrossRef30.Ocando-Mavarez E, Rosales M, Silva N (1998) Heteroatom Chem 9:253CrossRef31.Ocando-Mavarez E, Ascanio J, González T, Atencio R, Rosales M, Silva N (2003) Acta Cryst E59:m63332.Garcia JM, Coll DS, Ocando-Mavarez E, Ascanio J, Pekerar S, Atencio R, González T, Briceño A, Avila E, Rosales M (2014) Inorg Chim Acta 414:250CrossRef33.Casado J, López-Quintela MA, Lorenzo-Barral FM (1986) J Chem Ed 63:450CrossRef34.Brunner E (1985) J Chem Eng Data 30:269CrossRef35.Young CL (ed) (1981) Solubility data series, vol 5/6. Pergamon, Oxford, pp 176–42036.Crabtree RH, Anton DR (1983) Organometallics 2:855CrossRef37.Allen K, Bruck M, Gray S, Kingsborough R, Smith D, Weller K, Wigley D (1995) Polyhedron 14:3315CrossRef About this Article Title Kinetics and mechanisms of homogeneous catalytic reactions: Part 13. Regioselective reduction of quinoline catalysed by Rh(acac)(CO)[P(tBu)(CH2CH=CH2)2] Journal Transition Metal Chemistry Volume 41, Issue 4 , pp 467-473 Cover Date2016-05 DOI 10.1007/s11243-016-0042-7 Print ISSN 0340-4285 Online ISSN 1572-901X Publisher Springer International Publishing Additional Links Register for Journal Updates Editorial Board About This Journal Manuscript Submission Topics Catalysis Physical Chemistry Inorganic Chemistry Industry Sectors Materials & Steel Chemical Manufacturing IT & Software Telecommunications Aerospace Oil, Gas & Geosciences Authors Merlin Rosales (1) Karely Molina (1) Regina Vallejo (1) Edgar Ocando-Mavárez (2) Author Affiliations 1. Laboratorio de Química Inorgánica, Departamento de Química, Facultad Experimental de Ciencias, Universidad del Zulia (L.U.Z.), Apdo. 526, Maracaibo, Venezuela 2. Centro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apdo. 21827, Caracas, 1020, Venezuela Continue reading... To view the rest of this content please follow the download PDF link above.

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