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    المساهمون: University of Michigan

    المصدر: Langmuir ; volume 31, issue 18, page 5050-5056 ; ISSN 0743-7463 1520-5827

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    المساهمون: Department of Chemistry and Macromolecular Science and Engineering Program, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109‐1055, USA, Department of Chemistry and Macromolecular Science and Engineering Program, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109‐1055, USA.

    وصف الملف: application/pdf

    Relation: Bryan, Zachary J.; Smith, Mitchell L.; McNeil, Anne J. (2012). "Chain‐Growth Polymerization of Aryl Grignards Initiated by a Stabilized NHC‐Pd Precatalyst." Macromolecular Rapid Communications 33(9): 842-847.; https://hdl.handle.net/2027.42/92031; Macromolecular Rapid Communications; For recent reviews, see:a) C. Valente, S. Çalimsiz, K. H. Hoi, D. Mallik, M. Sayah, M. G. Organ, Angew. Chem. Int. Ed. 2012, 51, 2; b) M. G. Organ, G. A. Chass, D.‐C. Fang, A. C. Hopkinson, C. Valente, Synthesis 2008, 17, 2776.; M. Verswyvel, P. Verstappen, L. De Cremer, T. Verbiest, G. Koeckelberghs, J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 5339.; V. Senkovskyy, R. Tkachov, H. Komber, M. Sommer, M. Heuken, B. Voit, W. T. S. Huck, V. Kataev, A. Petr, A. Kiriy, J. Am. Chem. Soc. 2011, 133, 19966.; a) C. J. O'Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J. 2006, 12, 4743; b) M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 4749; c) M. G. Organ, M. Abdel‐Hadi, S. Avola, N. Hadei, J. Nasielski, C. J. O'Brien, C. Valente, Chem. Eur. J. 2007, 13, 150.; I. Larrosa, C. Somoza, A. Banquy, S. M. Goldup, Org. Lett. 2011, 13, 146.; a) M.‐T. Chen, D. A. Vicic, M. L. Turner, O. Navarro, Organometallics 2011, 30, 5052; b) See also, ref. 23.; A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 13944; See also: A. H. Roy, J. F. Hartwig, Organometallics 2004, 23, 1533.; a) S. Wu, L. Bu, L. Huang, X. Yu, Y. Han, Y. Geng, F. Wang, Polymer 2009, 50, 6245; b) R. Miyakoshi, A. Yokoyama, T. Yokozawa, Chem. Lett. 2008, 37, 1022; c) A. Yokoyama, A. Kato, R. Miyakoshi, T. Yokozawa, Macromolecules 2008, 41, 7271; e) See also, ref 3f.; M. C. Stefan, A. E. Javier, I. Osaka, R. D. McCullough, Macromolecules 2009, 42, 30.; Note that the radical‐based mechanisms have been proposed when iPrI is generated in situ. For reference, see:a) M. Kienle, P. Knochel, Org. Lett. 2010, 12, 2702; b) G. Manolikakes, P. Knochel, Angew. Chem. Int. Ed. 2009, 48, 205.; For example, see ref. 1b.; a) J.‐P. Lamps, J.‐M. Catala, Macromolecules. 2011, 44, 7962; b) See also, ref 21a.; Excess iPrMgCl (or tBuMgCl) can be detrimental. For example, see: R. H. Lohwasser, M. Thelakkat, Macromolecules 2011, 44, 3388.; a) L. Shi, Y. Chu, P. Knochel, H. Mayr, Org. Lett. 2009, 11, 3502; b) L. Shi, Y. Chu, P. Knochel, H. Mayr, J. Org. Chem. 2009, 74, 2760.; J. Nasielski, N. Hadei, G. Achonduh, E. A. B. Kantchev, C. J. O'Brien, A. Lough, M. G. Organ, Chem. Eur. J. 2010, 16, 10844.; a) E. L. Lanni, A. J. McNeil, Macromolecules. 2010, 43, 8039; b) E. L. Lanni, A. J. McNeil, J. Am. Chem. Soc. 2009, 131, 16573; c) See also, ref. 8.; a) R. Tkachov, V. Senkovskyy, H. Komber, A. Kiriy, Macromolecules. 2011, 44, 2006; b) R. Tkachov, V. Senkovskyy, H. Komber, J.‐U. Sommer, A. Kiriy, J. Am. Chem. Soc. 2010, 132, 7803; c) T. Beryozkina, V. Senkovskyy, E. Kaul, A. Kiriy, Macromolecules 2008, 41, 7817; d) R. Miyakoshi, A. Yokoyama, T. Yokozawa, J. Am. Chem. Soc. 2005, 127, 17542; e) M. C. Iovu, E. E. Sheina, R. R. Gil, R. D. McCullough, Macromolecules 2005, 38, 8649.; Unusually selective difunctionalizations have previously been observed with other Pd catalysts. Similar mechanisms have been proposed. For examples, see:a) S. K. Weber, F. Galbrecht, U. Scherf, Org. Lett. 2006, 8, 4039; b) D. J. Sinclair, M. S. Sherburn, J. Org. Chem. 2005, 70, 3730; c) C.‐G. Dong, Q.‐S. Hu, J. Am. Chem. Soc. 2005, 127, 10006.; a) E. E. Sheina, J. Liu, M. C. Iovu, D. W. Laird, R. D. McCullough, Macromolecules 2004, 37, 3526; b) A. Yokoyama, R. Miyakoshi, T. Yokozawa, Macromolecules 2004, 37, 1169; c) R. Miyakoshi, A. Yokoyama, T. Yokozawa, Macromol. Rapid Commun. 2004, 25, 1663.; For recent reviews, see:a) A. Kiriy, V. Senkovskyy, M. Sommer, Macromol. Rapid Commun. 2011, 32, 1503; b) K. Okamoto, C. K. Luscombe, Polym. Chem. 2011, 2, 2424.; For recent examples of block copolymers prepared via this method, see:a) M. Verswyvel, F. Monnaie, G. Koeckelberghs, Macromolecules 2011, 44, 9489; b) J. Kim, A. Siva, I. Y. Song, T. Park, Polymer. 2011, 52, 3704; c) T. Higashihara, K. Ohshimizu, Y. Ryo, T. Sakurai, A. Takahashi, S. Nojima, M. Ree, M. Ueda, Polymer 2011, 52, 3687; d) K. Ohshimizu, A. Takahashi, T. Higashihara, M. Ueda, J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2709; e) J. Hollinger, A. A. Jahnke, N. Coombs, D. S. Seferos, J. Am. Chem. Soc. 2010, 132, 8546; f) K. Van den Bergh, I. Cosemans, T. Verbiest, G. Koeckelberghs, Macromolecules 2010, 43, 3794; g) A. E. Javier, S. R. Varshney, R. D. McCullough, Macromolecules 2010, 43, 3233; h) S. Miyanishi, Y. Zhang, K. Tajima, K. Hashimoto, Chem. Commun. 2010, 46, 6723.; J. R. Locke, A. J. McNeil, Macromolecules 2010, 43, 8709.; For a recent review, see: N. Marshall, S. K. Sontag, J. Locklin, Chem. Commun. 2011, 47, 5681.; For recent examples, see:a) N. Doubina, S. A. Paniagua, A. V. Soldatova, A. K. Y. Jen, S. R. Marder, C. K. Luscombe, Macromolecules 2011, 44, 512; b) A. Smeets, P. Willot, J. De Winter, P. Gerbaux, T. Verbiest, G. Koeckelberghs, Macromolecules 2011, 44, 6017.; For a recent example of an non‐phosphine based Ni‐catalyst, see: H. D. Magurudeniya, P. Sista, J. K. Westbrook, T. E. Ourso, K. Nguyen, M. C. Maher, M. G. Alemseghed, M. C. Biewer, M. C. Stefan, Macromol. Rapid Commun. 2011, 32, 1748.; E. L. Lanni, J. R. Locke, C. M. Gleave, A. J. McNeil, Macromolecules 2011, 44, 5136.; S. R. Lee, Z. J. Bryan, A. M. Wagner, A. J. McNeil, Chem. Sci. 2012, DOI:10.1039/C2SC00005A.; a) A. R. Chianese, X. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663; b) W. A. Herrmann, J. Schütz, G. D. Frey, E. Herdtweck, Organometallics 2006, 25, 2437.; For recent reviews, see:a) G. C. Fortman, S. P. Nolan, Chem. Soc. Rev. 2011, 40, 5151; b) S. Díez‐González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612; c) E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. Int. Ed. 2007, 46, 2768.; S. Tamba, K. Shono, A. Sugie, A. Mori, J. Am. Chem. Soc. 2011, 133, 9700.; a) T. Yokozawa, R. Suzuki, M. Nojima, Y. Ohta, A. Yokoyama, Macromol. Rapid Commun. 2011, 32, 801; b) E. Elmalem, A. Kiriy, W. T. S. Huck, Macromolecules 2011, 44, 9057; c) T. Yokozawa, H. Kohno, Y. Ohta, A. Yokoyama, Macromolecules 2010, 43, 7095; d) W. Huang, L. Su, Z. Bo, J. Am. Chem. Soc. 2009, 131, 10348; e) T. Beryozkina, K. Boyko, N. Khanduyeva, V. Senkovskyy, M. Horecha, U. Oertel, F. Simon, M. Stamm, A. Kiriy, Angew. Chem. Int. Ed. 2009, 48, 2695; f) A. Yokoyama, H. Suzuki, Y. Kubota, K. Ohuchi, H. Higashimura, T. Yokozawa, J. Am. Chem. Soc. 2007, 129, 7236.; R. Grisorio, G. P. Suranna, P. Mastrorilli, Chem. Eur. J. 2010, 16, 8054.

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