ACS Catalysis
Research Article
(8) Liu, D.; Zhang, Y.; Chen, E. Y.-X. Green Chem. 2012, 14, 2738−
2746.
system than the Silica-g-[BI]-C12 + base system, which can be
attributed to the fact that the NHC derived from the
benzimidazolium salt carrying sterically more demanding
substituents on the nitrogen atoms exhibits better catalytic
performance in both homogeneous and heterogeneous catalyst
systems.
(9) Liu, D.; Chen, E. Y.-X. ChemSusChem 2013, 6, 2236−2239.
(10) Liu, D.; Chen, E. Y. X. ACS Catal. 2014, 4, 1302−1310.
(11) Wegenhart, B. L.; Yang, L.; Kwan, S. C.; Harris, R.; Kenttamaa,
H. I.; Abu-Omar, M. M. ChemSusChem 2014, 7, 2742−2747.
(12) (a) Kluger, R.; Tittmann, K. Chem. Rev. 2008, 108, 1797−1833.
(b) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719−3726. (c) Breslow,
R. J. Am. Chem. Soc. 1957, 79, 1762−1763.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
(13) (a) Berkessel, A.; Yatham, V. R.; Elfert, S.; Neudorfl, J.-M.
̈
S
Angew. Chem., Int. Ed. 2013, 52, 11158−11162. (b) Maji, B.; Mayr, H.
Angew. Chem., Int. Ed. 2013, 52, 11163−11167. (c) Berkessel, A.;
Elfert, S.; Yatham, V. R.; Neudorfl, M.-M.; Schlorer, N. E.; Teles, J. H.
̈
̈
1H and 13C NMR spectra of the intermediates and
Angew. Chem., Int. Ed. 2012, 51, 12370−12374.
(14) Selected reviews: (a) Flanigan, D. M.; Romanov-Michailidis, F.;
White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307. (b) Ryan, S. J.;
Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906−4917.
(c) Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314−
325. (d) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511−3522.
(e) Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182−
1195. (f) Moore, J. L.; Rovis, T. Top. Curr. Chem. 2009, 291, 77−144.
AUTHOR INFORMATION
Corresponding Author
■
Notes
́
(g) Marion, N.; Díez-Gonzalez, S.; Nolan, S. P. Angew. Chem., Int. Ed.
The authors declare no competing financial interest.
2007, 46, 2988−3000. (h) Enders, D.; Niemeier, O.; Henseler, A.
Chem. Rev. 2007, 107, 5606−5655. (i) Bourissou, D.; Guerret, O.;
Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39−91.
ACKNOWLEDGMENTS
■
This work was supported by Sekisui Chemical Co., Ltd. LW
thanks Sekisui Chemical for a postdoctoral fellowship, and we
thank Mr. Yuji Eguchi for helpful discussions.
́
(15) (a) Kabro, A.; Escudero-Adan, E. C.; Grushin, V. V.; van
Leeuwen, P. W. N. M. Org. Lett. 2012, 14, 4014−4017. (b) Shimakawa,
Y.; Morikawa, T.; Sakaguchi, S. Tetrahedron Lett. 2010, 51, 1786−
1789. (c) Hashmi, A. S. K.; Wolfle, M.; Teles, J. H.; Frey, W. Synlett
̈
2007, 2007, 1747−1752. (d) Enders, D.; Kallfass, U. Angew. Chem., Int.
Ed. 2002, 41, 1743−1745. (e) Lee, C. K.; Kim, M. S.; Gong, J. S.; Lee,
I.-S. H. J. Heterocycl. Chem. 1992, 29, 149−153. (f) Stetter, H.;
Ramsch, R. Y.; Kuhlmann, H. Synthesis 1976, 1976, 733−735.
(16) Zang, H.; Chen, E. Y. X. Int. J. Mol. Sci. 2015, 16, 7143−7158.
(17) (a) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F.
Nature 2014, 510, 485−496. (b) Benhamou, L.; Chardon, E.; Lavigne,
G.; Bellemin-Laponnaz, S.; Cesar, V. Chem. Rev. 2011, 111, 2705−
2733. (c) de Fremont, P.; Marion, N.; Nolan, S. P. Coord. Chem. Rev.
2009, 253, 862−892.
REFERENCES
■
(1) Selected reviews: (a) Alonso, D. M.; Wettstein, S. G.; Dumesic, J.
A. Green Chem. 2013, 15, 584−595. (b) Gallezot, P. Chem. Soc. Rev.
2012, 41, 1538−1558. (c) Alonso, D. M.; Bond, J. Q.; Dumesic, J. A.
Green Chem. 2010, 12, 1493−1513. (d) Corma, A.; Iborra, S.; Velty, A.
Chem. Rev. 2007, 107, 2411−2502. (e) Huber, G. W.; Corma, A.
Angew. Chem., Int. Ed. 2007, 46, 7184−7201. (f) Huber, G. W.; Iborra,
S.; Corma, A. Chem. Rev. 2006, 106, 4044−4098.
(2) Selected reviews: (a) Wang, T.; Nolte, M. W.; Shanks, B. H.
Green Chem. 2014, 16, 548−572. (b) Saha, B.; Abu-Omar, M. M.
Green Chem. 2014, 16, 24−38. (c) Teong, S. P.; Yi, G.; Zhang, Y.
Green Chem. 2014, 16, 2015−2026. (d) van Putten, R.-J.; van der
Waal, J. C.; de Jong, E.; Rasrendra, C. B.; Heeres, H. J.; de Vries, J. G.
Chem. Rev. 2013, 113, 1499−1597. (e) Lange, J.-P.; van der Heide, E.;
van Buijtenen, J.; Price, R. ChemSusChem 2012, 5, 150−166.
(f) Rosatella, A. A.; Simeonov, S. P.; Frade, R. F. M.; Afonso, C. A.
M. Green Chem. 2011, 13, 754−793. (g) Zakrzewska, M. E.; Bogel-
Łukasik, E.; Bogel-Łukasik, R. Chem. Rev. 2011, 111, 397−417.
(18) Droge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940−
6952.
(19) (a) Iwamoto, K.-i.; Kimura, H.; Oike, M.; Sato, M. Org. Biomol.
Chem. 2008, 6, 912−915. (b) Iwamoto, K.-I.; Hamaya, M.; Hashimoto,
N.; Kimura, H.; Suzuki, Y.; Sato, M. Tetrahedron Lett. 2006, 47, 7175−
7177.
(20) Powell, A. B.; Suzuki, Y.; Ueda, M.; Bielawski, C. W.; Cowley, A.
H. J. Am. Chem. Soc. 2011, 133, 5218−5220.
(21) (a) Coupillaud, P.; Pinaud, J.; Guidolin, N.; Vignolle, J.; Fevre,
M.; Veaudecrenne, E.; Mecerreyes, D.; Taton, D. J. Polym. Sci., Part A:
Polym. Chem. 2013, 51, 4530−4540. (b) Pinaud, J.; Vignolle, J.;
Gnanou, Y.; Taton, D. Macromolecules 2011, 44, 1900−1908.
(22) Seo, U. R.; Chung, Y. K. RSC Adv. 2014, 4, 32371−32374.
(23) Castells, J.; Dunach, E.; Geijo, F.; Pujol, G.; Segura, P. M. Isr. J.
Chem. 1978, 17, 278−283.
(h) Stahlberg, T.; Fu, W.; Woodley, J. M.; Riisager, A. ChemSusChem
̊
2011, 4, 451−458. (i) James, O. O.; Maity, S.; Usman, L. A.; Ajanaku,
K. O.; Ajani, O. O.; Siyanbola, T. O.; Sahu, S.; Chaubey, R. Energy
Environ. Sci. 2010, 3, 1833−1850. (j) Bozell, J. J.; Petersen, G. R. Green
Chem. 2010, 12, 539−554. (k) Top Value Added Chemicals from
Biomass; Werpy, T.; Petersen, G., Eds.; U.S. Department of Energy
(DOE) report: DOE/GO-102004-1992, 2004.
(24) Storey, J. M. D.; Williamson, C. Tetrahedron Lett. 2005, 46,
7337−7339.
(25) Zhang, Q.; Luo, J.; Wei, Y. Green Chem. 2010, 12, 2246−2254.
(26) Bohm, V. P. W.; Herrmann, W. A. Angew. Chem., Int. Ed. 2000,
39, 4036−4038.
(3) (a) King, A. E.; Brooks, T. J.; Tian, Y.-H.; Batista, E. R.; Sutton,
A. D. ACS Catal. 2015, 5, 1223−1226. (b) Sutton, A. D.; Waldie, F.
D.; Wu, R.; Schlaf, M.; Silks, L. A., III; Gordon, J. C. Nat. Chem. 2013,
5, 428−432.
(4) (a) Wegenhart, B. L.; Liu, S.; Thom, M.; Stanley, D.; Abu-Omar,
M. M. ACS Catal. 2012, 2, 2524−2530. (b) Balakrishnan, M.; Sacia, E.
R.; Bell, A. T. Green Chem. 2012, 14, 1626−1634. (c) Corma, A.; de la
Torre, O.; Renz, M. Energy Environ. Sci. 2012, 5, 6328−6344.
(d) Corma, A.; de la Torre, O.; Renz, M.; Villandier. Angew. Chem., Int.
Ed. 2011, 50, 2375−2378.
(5) Huber, G. W.; Chheda, J. N.; Barrett, C. J.; Dumesic, J. A. Science
2005, 308, 1446−1450.
(6) Huang, Y.-B.; Yang, Z.; Dai, J.-J.; Guo, Q.-X.; Fu, Y. RSC Adv.
2012, 2, 11211−11214.
(7) Liu, D.; Chen, E. Y.-X. Green Chem. 2014, 16, 964−981.
6917
ACS Catal. 2015, 5, 6907−6917