Communication
through electron transfer but not heterolysis. The alkylation of
the carbocations mainly occurs with dG and dC. This work pro-
vides two novel examples of photoinduced radical formation
and conversion to a carbocation from a bisaryl derivative that
efficiently forms DNA interstrand cross-link products.
Am. Chem. Soc. 2008, 130, 10299–10306; c) X. Weng, L. Ren, L. Weng, J.
Huang, S. Zhu, X. Zhou, L. Weng, Angew. Chem. Int. Ed. 2007, 46, 8020–
8023; Angew. Chem. 2007, 119, 8166–8169; d) S. Cao, Y. Wang, X. Peng,
Chemistry 2012, 18, 3850–3854; e) S. Cao, Y. Wang, X. Peng, J. Org.
Chem. 2014, 79, 501–508.
[8] a) S. S. Pan, T. Iracki, N. R. Bachur, Mol. Pharmacol. 1986, 29, 622–628;
b) M. Tomasz, R. Lipman, D. Chowdary, J. Pawlak, G. L. Verdine, K. Naka-
nishi, Science 1987, 235, 1204–1208.
[
9] a) P. Wang, R. Liu, X. Wu, H. Ma, X. Cao, P. Zhou, J. Zhang, X. Weng, X. L.
Zhang, J. Qi, X. Zhou, L. Weng, J. Am. Chem. Soc. 2003, 125, 1116 – 1117;
b) S. Colloredo-Mels, F. Doria, D. Verga, M. Freccero, J. Org. Chem. 2006,
Acknowledgements
This work was supported by the National Cancer Institute -
7
1, 3889–3895; c) M. Di Antonio, F. Doria, S. N. Richter, C. Bertipaglia, M.
Mella, C. Sissi, M. Palumbo, M. Freccero, J. Am. Chem. Soc. 2009, 131,
3132–13141; d) D. Verga, M. Nadai, F. Doria, C. Percivalle, M. Di Anto-
nio, M. Palumbo, S. N. Richter, M. Freccero, J. Am. Chem. Soc. 2010, 132,
4625–14637; e) S. N. Richter, S. Maggi, S. C. Mels, M. Palumbo, M. Frec-
cero, J. Am. Chem. Soc. 2004, 126, 13973–13979.
1R15A152914-01, Great Milwaukee Foundation (Shaw Scientist
1
Award), UWM Research Foundation Catalyst Grant, and Re-
search Growth Initiative.
1
[
10] a) Q. Zhang, Y. Wang, J. Am. Chem. Soc. 2003, 125, 12795–12802; b) G.
Lin, L. Li, Angew. Chem. Int. Ed. 2013, 52, 5594–5598; Angew. Chem.
Keywords: carbocations · DNA cross-linking · naphthalene
boronates · photochemistry · photoactivation · radicals
2
013, 125, 5704–5708; c) L. Weng, S. M. Horvat, C. H. Schiesser, M. M.
Greenberg, Org. Lett. 2013, 15, 3618–3621; d) Y. Han, W. Chen, Y.
Kuang, H. Sun, Z. Wang, X. Peng, Chem. Res. Toxicol. 2015, 28, 919–926;
e) F. Doria, M. Nadai, M. Folini, M. Scalabrin, L. Germani, G. Sattin, M.
Mella, M. Palumbo, N. Zaffaroni, D. Fabris, M. Freccero, S. N. Richter,
Chem. Eur. J. 2013, 19, 78–81; f) M. Nadai, F. Doria, L. Germani, S. N.
Richter, M. Freccero, Chem. Eur. J. 2015, 21, 2330–2334; g) Y. Wang, S.
Liu, Z. Lin, Y. Fan, Y. Wang, X. Peng, Org. Lett. 2016, 18, 2544–2547.
11] a) A. R. Lippert, G. C. Van de Bittner, C. J. Chang, Acc. Chem. Res. 2011,
[
1] a) F. Fakhari, S. E. Rokita, Nat.Commun. 2014, 5, 5591; b) M. Freccero,
Mini-Rev. Org. Chem. 2004, 1, 403–415; c) M. M. Haque, H. Sun, S. Liu, Y.
Wang, X. Peng, Angew. Chem. Int. Ed. 2014, 53, 7001–7005; Angew.
Chem. 2014, 126, 7121–7125.
[
2] a) D. Bastia, S. Zzaman, G. Krings, M. Saxena, X. Peng, M. M. Greenberg,
Proc. Natl. Acad. Sci. USA 2008, 105, 12831–12836; b) S. Cao, X. Peng,
Curr. Org. Chem. 2014, 18, 70–85; c) D. M. Noll, T. M. Mason, P. S. Miller,
Chem. Rev. 2006, 106, 277–301; d) X. Peng, A. K. Ghosh, B. Van Houten,
M. M. Greenberg, Biochemistry 2010, 49, 11–19; e) M. W. Weng, Y.
Zheng, V. P. Jasti, E. Champeil, M. Tomasz, Y. Wang, A. K. Basu, M. S.
Tang, Nucleic Acids Res. 2010, 38, 6976–6984.
[
4
1
4, 793–804; b) B. C. Dickinson, C. J. Chang, J. Am. Chem. Soc. 2008,
30, 9638–9639.
[
12] W. Chen, Y. Han, X. Peng, Chemistry 2014, 20, 7410–7418.
13] W. Chen, K. Balakrishnan, Y. Kuang, Y. Han, M. Fu, V. Gandhi, X. Peng, J.
Med. Chem. 2014, 57, 4498–4510.
[
[3] a) K. M. Johnson, Z. D. Parsons, C. L. Barnes, K. S. Gates, J. Org. Chem.
2
014, 79, 7520–7531; b) Y. Kuang, K. Balakrishnan, V. Gandhi, X. Peng, J.
[
[
14] S. Cao, R. Christiansen, X. Peng, Chemistry 2013, 19, 9050–9058.
15] a) M. C. Biewer, C. R. Behn, M. S. Platz, A. Despres, E. Migirdicyan, J. Am.
Chem. Soc. 1991, 113, 616–620; b) N. Bi, M. Ren, Q. Song, Synth.
Commun. 2010, 40, 2617–2623.
Am. Chem. Soc. 2011, 133, 19278–19281.
[
4] a) J. Woo, P. B. Hopkins, J. Am. Chem. Soc. 1991, 113, 5457–5459; b) K.
Fujimoto, A. Yamada, Y. Yoshimura, T. Tsukaguch, T. Sakamoto, J. Am.
Chem. Soc. 2013, 135, 16161–16167; c) M. Takasugi, A. Guendouz, M.
Chassignol, J. L. Decout, J. Lhomme, N. T. Thuong, C. Hꢁlꢂne, Proc. Natl.
Acad. Sci. USA 1991, 88, 5602.
[
[
16] S. Murarka, S. Wertz, A. Studer, Chimia 2012, 66, 413–417.
17] a) Y. Zeng, Y. Wang, Nucleic Acids Res. 2006, 34, 6521–6529; b) Y. Zeng,
Y. Wang, J. Am. Chem. Soc. 2004, 126, 6552–6553; c) H. Hong, Y. Wang,
J. Am. Chem. Soc. 2005, 127, 13969–13977.
[
[
[
5] a) P. Wang, Y. Song, L. Zhang, H. He, X. Zhou, Curr. Med. Chem. 2005, 12,
2
893–2913; b) S. Cao, X. H. Peng, Curr. Org. Chem. 2014, 18, 70–85;
[
18] a) K. Haraguchi, M. O. Delaney, C. J. Wiederholt, A. Sambandam, Z. Han-
tosi, M. M. Greenberg, J. Am. Chem. Soc. 2002, 124, 3263–3269; b) A. M.
Maxam, W. Gilbert, Methods Enzymol. 1980, 65, 499–560.
c) C. Percivalle, F. Doria, M. Freccero, Curr. Org. Chem. 2014, 18, 19–43.
6] a) W. F. Veldhuyzen, P. Pande, S. E. Rokita, J. Am. Chem. Soc. 2003, 125,
1
4005–14013; b) H. Wang, S. E. Rokita, Angew. Chem. Int. Ed. 2010, 49,
957–5960; Angew. Chem. 2010, 122, 6093–6096.
5
7] a) I. S. Hong, M. M. Greenberg, J. Am. Chem. Soc. 2005, 127, 10510–
0511; b) X. Peng, I. S. Hong, H. Li, M. M. Seidman, M. M. Greenberg, J.
Received: April 6, 2016
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