Organic Letters
Letter
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(f) Dimitrijevic, E.; Kvak, O.; Taylor, M. S. Chem. Commun. 2010, 46,
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9025. (g) Mele, A.; Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. J.
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(21) (a) Okumura, S.; Lin, C.-H.; Takeda, Y.; Minakata, S. J. Org. Chem.
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(22) (a) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.,
Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002. (b) Jiang, X.;
Wang, R. Chem. Rev. 2013, 113, 5515.
(8) (a) Gilday, L. C.; Lang, T.; Caballero, A.; Costa, P. J.; Fel
Beer, P. D. Angew. Chem., Int. Ed. 2013, 52, 4356. (b) Caballero, A.;
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Int. Ed. 2012, 51, 1876. (c) Serpell, C. J.; Kilah, N. L.; Costa, P. J.; Felix,
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ix, V.;
(23) Walter, S. M.; Kniep, F.; Rout, L.; Schmidtchen, F. P.; Herdtweck,
E.; Huber, S. M. J. Am. Chem. Soc. 2012, 134, 8507.
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(24) For the synthetic procedures, see the Supporting Information.
(25) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
(26) For the full titration experiments, see the Supporting Information.
(27) For a review on cation−π interactions, see: (a) Ma, J. C.;
Dougherty, D. A. Chem. Rev. 1997, 97, 1303. For reports on the
cation−π interactions between imidazolium salts and aromatic
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V.; Beer, P. D. Angew. Chem., Int. Ed. 2010, 49, 5322. (d) Kilah, N. L.;
Wise, M. D.; Serpell, C. J.; Thompson, A. L.; White, N. G.; Christensen,
K. E.; Beer, P. D. J. Am. Chem. Soc. 2010, 132, 11893. (e) You, L.-Y.;
Chen, S.-G.; Zhao, X.; Liu, Y.; Lan, W.-X.; Zhang, Y.; Lu, H.-J.; Cao, C.-
Y.; Li, Z.-T. Angew. Chem., Int. Ed. 2012, 51, 1657. (f) Takeuchi, T.;
Minato, Y.; Takase, M.; Shinmori, H. Tetrahedron Lett. 2005, 46, 9025.
(9) (a) Jentzsch, A. V.; Matile, S. J. Am. Chem. Soc. 2013, 135, 5302.
(b) Jentzsch, A. V.; Emery, E.; Mareda, J.; Nayak, S. K.; Metrangolo, P.;
Resnati, G.; Sakai, N.; Matile, S. Nat. Commun. 2012, 3, 905. (c) Jentzsch,
A. V.; Emery, D.; Mareda, J.; Metrangolo, P.; Resnati, G.; Matile, S.
Angew. Chem., Int. Ed. 2011, 50, 11675.
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compounds, see: (b) Gutel, T.; Santini, C. C.; Padua, A. A. H.; Fenet,
B.; Chauvin, Y.; Lopes, J. N. C.; Bayard, F.; Gomes, M. F. C.; Pensado, A.
S. J. Phys. Chem. B 2008, 113, 170. (c) Shimomura, T.; Takamuku, T.;
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(28) Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J.
Am. Chem. Soc. 2004, 126, 4366.
(29) This downfield shift of 13C NMR resonance of iodine-carrying
carbon is fully consistent with the behavior of other iodoimidazolium
salts reported in the literature (ref 14c and 16). Also, for the effect of XB
on 13C NMR resonances, see: (a) Glaser, R.; Chen, N.; Wu, H.; Knotts,
N.; Kaupp, M. J. Am. Chem. Soc. 2004, 126, 4412. (b) Rege, P. D.;
Malkina, O. L.; Goroff, N. S. J. Am. Chem. Soc. 2001, 124, 370.
(30) While the reaction did not proceed at all in the absence of catalyst
H, a trace amount of product 6a was detected when A was applied as a
catalyst.
(10) (a) Scholfield, M. R.; Zanden, C. M. V.; Carter, M.; Ho, P. S.
Protein Sci. 2013, 22, 139. (b) Hardegger, L. A.; Kuhn, B.; Spinnler, B.;
Anselm, L.; Ecabert, R.; Stihle, M.; Gsell, B.; Thoma, R.; Diez, J.; Benz,
J.; Plancher, J.-M.; Hartmann, G.; Banner, D. W.; Haap, W.; Diederich,
F. Angew. Chem., Int. Ed. 2011, 50, 314. (c) Parisini, E.; Metrangolo, P.;
Pilati, T.; Resnati, G.; Terraneo, G. Chem. Soc. Rev. 2011, 40, 2267.
(d) Lu, Y.; Wang, Y.; Zhu, W. Phys. Chem. Chem. Phys. 2010, 12, 4543.
(e) Kraut, D. A.; Churchill, M. J.; Dawson, P. E.; Herschlag, D. ACS
Chem. Biol. 2009, 4, 269. (f) Voth, A. R.; Khuu, P.; Oishi, K.; Ho, P. S.
Nat. Chem. 2009, 1, 74. (g) Voth, A. R.; Hays, F. A.; Ho, P. S. Proc. Natl.
Acad. Sci. U.S.A. 2007, 104, 6188. (h) Auffinger, P.; Hays, F. A.; Westhof,
E.; Ho, P. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789.
(11) (a) Bruckmann, A.; Pena, M. A.; Bolm, C. Synlett 2008, 900.
(b) He, W.; Ge, Y.-C.; Tan, C.-H. Org. Lett. 2014, 16, 3244.
(12) Coulembier, O.; Meyer, F.; Dubois, P. Polym. Chem. 2010, 1, 434.
(13) Kniep, F.; Jungbauer, S. H.; Zhang, Q.; Walter, S. M.; Schindler,
S.; Schnapperelle, I.; Herdweck, E.; Huber, S. M. Angew. Chem., Int. Ed.
2013, 52, 7028.
(14) As related leading works, the Huber group has demonstrated that
polyhalogenated heterocyclic onium salts serve as stoichiometric
activating reagents to abstract bromide in the SN1-type reactions of
activated organic halides; see: (a) Walter, S. M.; Kniep, F.; Herdtweck,
E.; Huber, S. M. Angew. Chem., Int. Ed. 2011, 50, 7187. (b) Kniep, F.;
Walter, S. M.; Herdtweck, E.; Huber, S. M. Chem.Eur. J. 2012, 18,
1306. (c) Kniep, F.; Rout, L.; Walter, S. M.; Bensch, H. K. V.; Jungbauer,
S. H.; Herdtweck, E.; Huber, S. M. Chem. Commun. 2012, 48, 9299.
(d) Castelli, R.; Schindler, S.; Walter, S. M.; Kniep, F.; Overkleeft, H. S.;
van der Marel, G. A.; Huber, S. M.; Codee, J. D. C. Chem.Asian J.
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2014, 9, 2095.
(15) Very recently, the Takemoto group reported an XB-donor-
induced semipinacol rearrangement via C−X bond cleavage; see: Tsuji,
N.; Kobayashi, Y.; Takemoto, Y. Chem. Commun. 2014, 50, 13691.
(16) Examples of supramolecular catalysts built up through XB have
also been reported; see: (a) Dordonne, S.; Crousse, B.; Bonnet-Delpon,
D.; Legros, J. Chem. Commun. 2011, 47, 5855. (b) Lindsay, V. N. G.; Lin,
W.; Charette, A. B. J. Am. Chem. Soc. 2009, 131, 16383.
(17) The Ishihara group has recently reported that XB-donors play an
important role in the activation of dihalogen species in an organo-
ccatalytic iodolactonization; see: Nakatsuji, H.; Sawamura, Y.; Sakakura,
A.; Ishihara, K. Angew. Chem., Int. Ed. 2014, 53, 6974.
(18) The formation of XB in the transition state of an enantioselective
organocatalytic alkylation of sulfenate anions is also suggested; see:
Zong, L.; Ban, X.; Kee, C. W.; Tan, C.-H. Angew. Chem., Int. Ed. 2014,
53, 11849.
(19) Dang, T. T.; Boeck, F.; Hintermann, L. J. Org. Chem. 2011, 76,
9353.
(20) Jungbauer, S. H.; Walter, S. M.; Schindler, S.; Rout, L.; Kniep, F.;
Huber, S. M. Chem. Commun. 2014, 50, 6281.
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Org. Lett. XXXX, XXX, XXX−XXX