Organic Letters
Letter
(3) For a comprehensive review on the halogen bond: (a) Cavallo,
G.; Metrangolo, P.; Milani, R.; Pilati, T.; Priimagi, A.; Resnati, G.;
Terraneo, G. Chem. Rev. 2016, 116, 2478−2601. For the recent
definition of XB recommended by IUPAC in 2013: (b) Desiraju, G.
R.; Ho, P. S.; Kloo, L.; Legon, A. C.; Marquardt, R.; Metrangolo, P.;
Politzer, P.; Resnati, G.; Rissanen, K. Pure Appl. Chem. 2013, 85,
1711−1713.
(4) Recent reviews: (a) Bulfield, D.; Huber, S. M. Chem. - Eur. J.
2016, 22, 14434−14450. (b) Zhao, Y.; Cotelle, Y.; Sakai, N.; Matile,
S. J. Am. Chem. Soc. 2016, 138, 4270−4277.
work will open interesting avenues to consider how to engage
electron donor−acceptor complexes enhanced by potential
halogen bonding for the engineering of unconventional
chemical reactions.
ASSOCIATED CONTENT
* Supporting Information
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sı
The Supporting Information is available free of charge at
(5) Bruckmann, A.; Pena, M. A.; Bolm, C. Synlett 2008, 6, 158−165.
(6) (a) Walter, S. M.; Kniep, F.; Herdtweck, E.; Huber, S. M. Angew.
Chem., Int. Ed. 2011, 50, 7187−7191. (b) Kniep, F.; Walter, S. M.;
Herdtweck, E.; Huber, S. M. Chem. - Eur. J. 2012, 18, 1306−1310.
(c) Sakakura, A.; Ukai, A.; Ishihara, K. Nature 2007, 445, 900−903.
(d) Walter, S. M.; Kniep, F.; Rout, L.; Schmidtchen, F. P.; Herdtweck,
E.; Huber, S. M. J. Am. Chem. Soc. 2012, 134, 8507−8512.
(e) Jungbauer, S. H.; Huber, S. M. J. Am. Chem. Soc. 2015, 137,
12110−12120. (f) Saito, M.; Tsuji, N.; Kobayashi, Y.; Takemoto, Y.
Org. Lett. 2015, 17, 3000−3003. (g) Saito, M.; Kobayashi, Y.;
Tsuzuki, S.; Takemoto, Y. Angew. Chem., Int. Ed. 2017, 56, 7653−
7657. (h) He, W.; Ge, Y.-C.; Tan, C.-H. Org. Lett. 2014, 16, 3244−
3247. (i) Takeda, Y.; Hisakuni, D.; Lin, C.-H.; Minakata, S. Org. Lett.
2015, 17, 318−321. (j) Chan, Y.-C.; Yeung, Y.-Y. Angew. Chem., Int.
Ed. 2018, 57, 3483−3487.
(7) (a) Kniep, F.; Jungbauer, S. H.; Zhang, Q.; Walter, S. M.;
Schindler, S.; Schnapperelle, I.; Herdtweck, E.; Huber, S. M. Angew.
Chem., Int. Ed. 2013, 52, 7028−7032. (b) Jungbauer, S. H.; Walter, S.
M.; Schindler, S.; Rout, L.; Kniep, F.; Huber, S. M. Chem. Commun.
2014, 50, 6281−6284. (c) Gliese, J.-P.; Jungbauer, S. H.; Huber, S. M.
Chem. Commun. 2017, 53, 12052−12055. (d) Dreger, A.; Engelage,
E.; Mallick, B.; Beer, P. D.; Huber, S. M. Chem. Commun. 2018, 54,
4013−4016.
Experimental procedure and characterization data for
AUTHOR INFORMATION
Corresponding Author
■
Wei Li − Department of Chemistry and Biochemistry, School of
Green Chemistry and Engineering, The University of Toledo,
Authors
Fan Wu − Department of Chemistry and Biochemistry, School of
Green Chemistry and Engineering, The University of Toledo,
Toledo, Ohio 43606, United States
Jeewani P. Ariyarathna − Department of Chemistry and
Biochemistry, School of Green Chemistry and Engineering, The
University of Toledo, Toledo, Ohio 43606, United States
Navdeep Kaur − Department of Chemistry and Biochemistry,
School of Green Chemistry and Engineering, The University of
Toledo, Toledo, Ohio 43606, United States
(8) For other visible-light-mediated processes based on the halogen
bond: (a) Wang, Y.; Wang, J.; Li, G.-X.; He, G.; Chen, G. Org. Lett.
2017, 19, 1442−1445. (b) Wang, R.; Guan, W.; Han, Z.-B.; Liang, F.;
Suga, T.; Bi, X.; Nishide, H. Org. Lett. 2017, 19, 2358−2361.
(9) (a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem.
2014, 57, 10257−10274. (b) Yi, H.; Zhang, G.; Wang, H.; Huang, Z.;
Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016−9085.
(10) For selected recent reviews: (a) Park, Y.; Kim, Y.; Chang, S.
Chem. Rev. 2017, 117, 9247−9301. (b) Du Bois, J. Org. Process Res.
Dev. 2011, 15, 758−762. (c) Davies, H. M. L. Angew. Chem., Int. Ed.
2006, 45, 6422−6425. (d) Davies, H. M. L.; Manning, J. R. Nature
2008, 451, 417−424. For examples of transition-metal-catalyzed
nitrene insertion for C−H aminations: (e) Roizen, J. L.; Harvey, M.
E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911−922. (f) Dequirez, G.;
Pons, V.; Dauban, P. Angew. Chem., Int. Ed. 2012, 51, 7384−7395.
(g) Chiappini, N. D.; Mack, J. B. C.; Du Bois, J. Angew. Chem., Int. Ed.
2018, 57, 4956−4959. (h) Hong, S. Y.; Park, Y.; Hwang, Y.; Kim, Y.
B.; Baik, M.-H.; Chang, S. Science 2018, 359, 1016−1021. (i) Clark, J.
R.; Feng, K.; Sookezian, A.; White, C. M. Nat. Chem. 2018, 10, 583−
591. (j) Prier, C. K.; Zhang, R. K.; Buller, A. R.; Brinkmann-Chen, S.;
Arnold, F. H. Nat. Chem. 2017, 9, 629−634. (k) Wu, X.; Yang, K.;
Zhao, Y.; Sun, H.; Li, G.; Ge, H. Nat. Commun. 2015, 6, 6462. For a
recent example of organocatalytic nitrene transfer for C−H
amination: (l) Combee, L. A.; Raya, B.; Wang, D.; Hilinski, M. K.
Chem. Sci. 2018, 9, 935−939.
(11) For selected examples of azidyl and hydrazine-based reagents:
(a) Sharma, A.; Hartwig, J. F. Nature 2015, 517, 600−604.
(b) Huang, X.; Bergsten, T. M.; Groves, J. T. J. Am. Chem. Soc.
2015, 137, 5300−5303. (c) Lu, H.; Subbarayan, V.; Tao, J.; Zhang, X.
P. Organometallics 2010, 29, 389−393. (d) Amaoka, Y.; Kamijo, S.;
Hoshikawa, T.; Inoue, M. J. Org. Chem. 2012, 77, 9959−9969. For a
example with NFSI: (e) Ni, Z.; Zhang, Q.; Xiong, T.; Zheng, Y.; Li,
Y.; Zhang, H.; Zhang, J.; Liu, Q. Angew. Chem., Int. Ed. 2012, 51,
1244−1247. (f) Bentley, K. W.; Dummit, K. A.; Van Humbeck, J. F.
Chem. Sci. 2018, 9, 6440−6445. (g) Hu, A.; Guo, J.-J.; Pan, H.; Zuo,
Z. Science 2018, 361, 668−672.
Nur-E Alom − Department of Chemistry and Biochemistry,
School of Green Chemistry and Engineering, The University of
Toledo, Toledo, Ohio 43606, United States
Maureen L. Kennell − Department of Chemistry and
Biochemistry, School of Green Chemistry and Engineering, The
University of Toledo, Toledo, Ohio 43606, United States
Omar H. Bassiouni − Department of Chemistry and
Biochemistry, School of Green Chemistry and Engineering, The
University of Toledo, Toledo, Ohio 43606, United States
Complete contact information is available at:
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We would like to dedicate this work to Prof. D. W. C.
MacMillan (Princeton Univ.) for his 52nd birthday. We thank
the Univ. of Toledo for a startup grant. We thank Dr. Y. W.
Kim (Univ. of Toledo) for NMR assistance. G.-S. S. Shyam
(Univ. of Toledo) and Z. (M.) Wang at Environmental
Analysis Service Center (Univ. of Cincinnati) are acknowl-
edged for collecting high-resolution mass spectrometry data.
REFERENCES
■
(1) (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88,
899−926. (b) Toste, F. D.; Sigman, M. S.; Miller, S. J. Acc. Chem. Res.
2017, 50, 609−615. (c) Neel, A. J.; Hilton, M. J.; Sigman, M. S.;
Toste, F. D. Nature 2017, 543, 637−646. (d) Davis, H. J.; Phipps, R.
J. Chem. Sci. 2017, 8, 864−877.
(2) Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad.
Sci. U. S. A. 2004, 101, 16789−16794.
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