Journal of the American Chemical Society
Communication
(12) Hayashi, T.; Hirate, S.; Kitayama, K.; Tsuji, H.; Torii, A.; Uozumi,
Y. Chem. Lett. 2000, 1272.
Notes
The authors declare no competing financial interest.
(13) Iwasawa, T.; Komano, T.; Tajima, A.; Tokunaga, M.; Obora, Y.;
Fujihara, T.; Tsuji, Y. Organometallics 2006, 25, 4465.
(14) PS-PPh3 was purchased from Biotage. Resin type, 1% cross-linked
poly(styrene-co-divinylbenzene); loading, 2.09 mmol/g (based on
uptake of benzylbromide); mean bead size, 123 μm, 100−200 mesh
(95% within).
ACKNOWLEDGMENTS
■
We thank Professors Yasushi Tsuji and Tetsuaki Fujihara (Kyoto
University) for providing phosphorus ligands L7 and L8. This
work was supported by CREST, Japan Science and Technology
Agency (JST).
REFERENCES
■
(1) (a) Lu, J.; Toy, P. H. Chem. Rev. 2009, 109, 815. (b) Piguet, C.;
Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005.
(c) Trindade, A. F.; Gois, P. M. P.; Afonso, C. A. M. Chem. Rev. 2009,
109, 418. (d) Wang, Z.; Chen, G.; Ding, K. Chem. Rev. 2009, 109, 322.
(e) Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 103, 3401.
(f) Itsuno, S., Ed.; Polymeric Ciral Catalyst Design and Chiral Polymer
Synthesis; Wiley: Weinheim, Germany, 2011. (g) Ding, K.; Uozumi, Y.,
Ed.; Handbook of Asymmetric Heterogeneous Catalysis; Wiley: Weinheim,
Germany, 2008.
(2) Poly(trityl methacrylate)-based system: (a) Reggelin, M.; Schultz,
M.; Holbach, M. Angew. Chem., Int. Ed. 2002, 41, 1614. (b) Reggelin, M.;
Doerr, S.; Klussmann, M.; Schultz, M.; Holbach, M. Proc. Natl. Acad. Sci.
U.S.A. 2004, 101, 5461. DNA-based system: (c) Boersma, A. J.; Feringa,
B. L.; Roelfes, G. Org. Lett. 2007, 9, 3647. (d) Roelfes, G.; Feringa, B. L.
̀
Angew. Chem., Int. Ed. 2005, 44, 3230. (e) Coquiere, D.; Feringa, B.;
Roelfes, G. Angew. Chem., Int. Ed. 2007, 46, 9308. (f) Boersma, A. J.;
Feringa, B. L.; Roelfes, G. Angew. Chem., Int. Ed. 2009, 48, 3346.
(g) Boersma, A. J.; Megens, R. P.; Feringa, B. L.; Roelfes, G. Chem. Soc.
Rev. 2010, 39, 2083. Poly(phenylacetylene)-based system: (h) Miyake,
G. M.; Iida, H.; Hu, H.-Y.; Tang, Z.; Chen, E. Y. X.; Yashima, E. J. Polym.
Sci. Polym. Chem. 2011, 49, 5192. Reviews: (i) Yashima, E.; Maeda, K.;
Iida, H.; Furusho, Y.; Nagai, K. Chem. Rev. 2009, 109, 6102. (j) Megens,
R. P.; Roelfes, G. Chem.Eur. J. 2011, 17, 8514.
(3) (a) Ohta, H.; Tokunaga, M.; Obora, Y.; Iwai, T.; Iwasawa, T.;
Fujihara, T.; Tsuji, Y. Org. Lett. 2007, 9, 89. (b) Fujihara, T.; Tomike, Y.;
Ohtake, T.; Terao, J.; Tsuji, Y. Chem. Commun. 2011, 47, 9699.
(4) (a) Yamamoto, T.; Yamada, T.; Nagata, Y.; Suginome, M. J. Am.
Chem. Soc. 2010, 132, 7899. (b) Yamamoto, T.; Suginome, M. Angew.
Chem., Int. Ed. 2009, 48, 539. (c) Yamamoto, T.; Akai, Y.; Nagata, Y.;
Suginome, M. Angew. Chem., Int. Ed. 2011, 50, 8844.
(5) For early studies on the synthesis and structure of poly(quinoxa-
line-2,3-diyl)s, see: (a) Ito, Y.; Ihara, E.; Murakami, M.; Shiro, M. J. Am.
Chem. Soc. 1990, 112, 6446. (b) Ito, Y.; Ihara, E.; Murakami, M. Angew.
Chem., Int. Ed. Engl. 1992, 31, 1509.
(6) For the development of the asymmetric synthesis of poly(quinoxa-
line-2,3-diyl)s, see: (a) Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am.
Chem. Soc. 1996, 118, 9188. (b) Ito, Y.; Miyake, T.; Hatano, S.; Shima,
R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880.
(c) Suginome, M.; Collet, S.; Ito, Y. Org. Lett. 2002, 4, 351.
(7) For the use of chiral organonickel initiators for asymmetric
polymerization of 1,2-diisocyanobenzenes, see: (a) Yamada, T.;
Noguchi, H.; Nagata, Y.; Suginome, M. J. Polym. Sci., Part A 2010, 48,
898. (b) Yamada, T.; Suginome, M. Macromolecules 2010, 43, 3999.
(8) Yamada, T.; Nagata, Y.; Suginome, M. Chem. Commun. 2010, 46, 4914.
(9) Significant enhancement of TON and TOF was achieved with
polymer-based catalysts bearing PEG side chains in palladium-catalyzed
allylic substitution reactions in water. Yamada, Y. M. A.; Sarkar, S. M.;
Uozumi, Y. J. Am. Chem. Soc. 2012, 134, 3190.
(10) (a) Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M. J. Am.
Chem. Soc. 2007, 129, 3518. (b) Ohmura, T.; Taniguchi, H.; Suginome,
M. Org. Lett. 2009, 11, 2880. Nonasymmetric version: (c) Suginome,
M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. Review on
catalytic silaboration: (d) Ohmura, T.; Suginome, M. Bull. Chem. Soc.
Jpn. 2009, 82, 29.
(11) Mn and Mw/Mn values (GPC, polystyrene standard) of the
polymer ligands are as follows. L1, Mn = 2.7 × 105, Mw/Mn = 1.20; L2,
Mn = 2.1 × 105, Mw/Mn = 1.31; L3, Mn = 1.8 × 105, Mw/Mn =1.52. See
the Supporting Information for details.
D
dx.doi.org/10.1021/ja303506k | J. Am. Chem. Soc. XXXX, XXX, XXX−XXX