10.1002/anie.201809454
Angewandte Chemie International Edition
COMMUNICATION
Electrochemical studies have disclosed that the styrene radical
cation intermediate is more likely to be trapped by styrene first on
the carbon electrode. On the other hand, the Pt electrode should
[14] a) L. J. Xiao, L. Cheng, W. M. Feng, M. L. Li, J. H. Xie, Q. L. Zhou, Angew.
Chem. Int. Ed. 2018, 57, 461–464; b) N. J. W. Straathof, S. E. Cramer, V.
Hessel, T. Noꢁl, Angew. Chem. Int. Ed. 2016, 55, 15549–15553; c) D. J.
Wilger, J.-M. M. Grandjean, T. R. Lammert, D. A. Nicewicz, Nat. Chem.
2014, 6, 720; d) V. R. Yatham, Y. Shen, R. Martin, Angew. Chem. Int. Ed.
2017, 56, 10915–10919.
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allow the intermediate to be captured by O2 −. This discovery is
informative for further research on electrolysis.
[15] a) J. P. Wan, Y. Gao, L. Wei, Chem. Asian J. 2016, 11, 2092–2102; b) A.
Rubinstein, P. J. Lozanao, J. J. Carbó, J. M. Poblet, R. Neumann, J. Am.
Chem. Soc. 2014, 136, 10941–10948; c) M. M. Hossain, S. G. Shyu,
Tetrahedron 2014, 70, 251–255; d) R. Lin, F. Chen, N. Jiao, Org. Lett.
2012, 14, 4158–4161; e) G. Z. Wang, X. L. Li, J. J. Dai, H. J. Xu, J. Org.
Chem. 2014, 79, 7220–7225; f) A. K. Singh, R. Chawla, L. D. S. Yadav,
Tetrahedron Lett. 2015, 56, 653–656; g) E. L. Clennan, G. I. Pan, Org.
Lett. 2003, 5, 4979–4982; h) K. Suga, K. Ohkubo, S. Fukuzumi, J. Phys.
Chem. A, 2003, 107, 4339–4346; i) Y. Deng, X. J. Wei, H. Wang, Y. Sun,
T. Noꢁl, X. Wang, Angew. Chem. Int. Ed. 2017, 56, 832–836; j) T. Wang,
N. Jiao, J. Am. Chem. Soc. 2013, 135, 11692–11695; k) X. Wu, A. P.
Davis, A. J. Fry, Org. Lett. 2007, 9, 5633-5636.
Acknowledgements
This work was partially supported by JSPS KAKENHI Grant
Numbers 15H04494, 17K19222 (to K.C.), 16H06193, and
17K19221 (to Y.O.).
Keywords: electrochemistry • styrenes • olefin cleavage •
tetrahydrofurans synthesis • electrode material
[1] a) M. Yan, Y. Kawamata, P. S. Baran, Chem. Rev. 2017, 117, 13230-
13319; b) J. I. Yoshida, A. Shimizu, R. Hayashi, Chem. Rev. 2018, 118,
4702–4730; c) N. Fu, G. S. Sauer, A. Saha, A. Loo, S. Lin, Science, 2017,
357, 575–579; d) S. Tang, S. Wang, Y. Liu, H. Cong, A. Lei, Angew. Chem.
Int. Ed. 2018, 57, 4737–4741; e) Z. W. Hou, Z. Y. Mao, H. B. Zhao, Y. Y.
Melcamu, X. Lu, J. Song, H. C. Xu, Angew. Chem. Int. Ed. 2016, 55, 9168–
9172; f) Y. F. Liang, R. Steinbock, A. Münch, D. Stalke, L. Ackermann,
Angew. Chem. Int. Ed. 2018, 57, 5384–5388.
[16] S. G. Van Ornum, R. M. Champeau, R. Pariza, Chem. Rev. 2006, 106,
2990–3001.
[17] a) N. L. Bauld, R. Pabon, J. Am. Chem. Soc. 1983, 105, 633-634; b) L.
Wang, F. Wu, J. Chen, D. A. Nicewicz, Y. Huang, Angew. Chem. Int. Ed.
2017, 56, 6896–6900; c) S. Lin, M. A. Ischay, C. G. Fry, T. P. Yoon, J.
Am. Chem. Soc. 2011, 133, 19350–19353; d) J. Zhao, J. L. Brosmer, Q.
Tang, Z. Yang, K. N. Houk, P. L. Diaconescu, O. Kwon, J. Am. Chem.
Soc. 2017, 139, 9807–9810; e) Y. Okada, Y. Yamaguchi, A. Ozaki, K.
Chiba, Chem. Sci. 2016, 7, 6387–6393.
[2] J. Kulisch, M. Nieger, F. Stecker, A. Fischer, S. R. Waldvogel, Angew.
Chem. Int. Ed. 2011, 50, 5564–5567.
[3] a) Y. Okada, K. Chiba, Chem. Rev. 2018, 118, 4592−4630. b) Y. Imada,
Y. Yamaguchi, N. Shida, Y. Okada, K. Chiba, Chem. Commun. 2017, 53,
3960–3963.
[18] a) R. J. Perkins, H. C. Xu, J. M. Campbell, K. D. Moeller, Beilstein J.
Org. Chem. 2013, 9, 1630-1636; b) Cai, C., Xu, H, Nat. Commun. 2018,
9, 3551.
[4] T. Gieshoff, D. Schollmeyer, S. R. Waldvogel, Angew. Chem. Int. Ed. 2016,
55, 9437–9440.
[19] R. B. Teponno, S. Kusari, M. Spiteller, Nat. Prod. Rep. 2016, 33, 1044-
1092.
[5] T. Shoji, S. Kim, K. Chiba, Angew. Chem. Int. Ed. 2017, 56, 4011–4014.
[6] a) A. Medici, P. Pedrini, A. De Battisti, G. Fantin, M. Fogagnolo, A. Guerrini,
Steroids, 2001, 66, 63–69; b) I. M. Malkowsky, U. Griesbach, H. Pütter, S.
R. Waldvogel, Eur. J. Org. Chem. 2006, 4569–4572; c) S. B. Beil, T. Mꢀller,
S. B. Sillart, P. Franzmann, A. Bomm, M. Holtkamp, U. Karst, W. Schade,
S. R. Waldvogel, Angew. Chem. Int. Ed. 2018, 57, 2450–2454.
[7] C. Gütz, M. Selt, M. Bänziger, C. Bucher, C. Römelt, N. Hecken, F. Gallou,
T. R. Galvão, S. R. Waldvogel, Chem. Eur. J. 2015, 21, 13878–13882.
[8] I. M. Malkowsky, C. E. Rommel, K. Wedeking, R. Fröhlich, K. Bergander,
M. Nieger, C. Quaiser, U. Griesbach, H. Pütter, S. R. Waldvogel, Eur. J.
Org. Chem. 2006, 241–245.
[20] CCDC 1861076 (trans-3c) and 1861075 (cis-9c) contain the
supplementary crystallographic data for this paper. These data are
provided free of charge by The Cambridge Crystallographic Data Center.
[21] Q. Li, C. Batchelor-Mcauley, N. S. Lawrence, R. S. Hartshorne, R. G.
Compton, J. Electroanal. Chem. 2013, 688, 328–335.
[22] M. Katz, P. Riemenschneider, H. Wendt, Electrochim. Acta, 1972, 17,
1595–1607.
[23] C. M. Cardona, W. Li, A. E. Kaifer, D. Stockdale, G. C. Bazan, Adv. Mater.
2011, 23, 2367–2371.
[24] M. Swart, T. V. D. Wijst, C. F. Guerra, F. M. Bickelhaupt, J. Mol. Model.
2007, 13, 1245–1257.
[9] Zhao, H. , Xu, P. , Song, J. and Xu, H. (2018), Cathode Material
Determines Product Selectivity for Electrochemical C–H
[25] a) U. Akbulut, J. E. Fernandez, R. L. Birke, J. Polym. Sci. Polym. Chem.
Ed. 1975, 13, 133–149; b) U. Akbulut, S. Eren, L. K. Toppare, Polymer,
1984, 25, 1028-1030.
Functionalization of Biaryl Ketoximes. Angew. Chem. Int. Ed.. Accepted
[10] M. C. Figueiredo, V. Trieu, S. Eiden, M. T. M. Koper, J. Am. Chem. Soc.
2017, 139, 14693–14698.
[26] a) M. Shao, P. Liu, R. R. Adzic, J. Am. Chem. Soc. 2006, 128, 7408–
7409; b) S. L. McLellan, Diss. Abs. (B), 1975, 36, 744.
[11] H. Seo, A. Liu, T. F. Jamison, J. Am. Chem. Soc. 2017, 139, 13969-13972.
[12] a) H. Huang, C. Yu, Y. Zhang, Y. Zhang, P. S. Mariano, W. Wang, J. Am.
Chem. Soc. 2017, 139, 9799–9802; b) F. Wu, L. Wang, J. Chen, D. A.
Nicewicz, Y. Huang, Angew. Chem. Int. Ed. 2018, 57, 2174–2178.
[13] a) M. Utsunomiya, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14286–
14287; b) K. Muñiz, L. Barreiro, R. M. Romero, C. Martínez, J. Am. Chem.
Soc. 2017, 139, 4354–4357.
[27] G. Burgbacher, H. J. Schafer, J. Am. Chem. Soc. 1979, 101, 7590-7593.
[28] T. Ozawa, A. Hanaki, H. Yamamoto, FEBS Lett. 1977, 74, 99–102.
[29] a) J. M. McCord, I. Fridovich, J. Biol. Chem. 1969, 244, 6049–6055; b)
D. Vasudevan, H. Wendt, J. Electroanal. Chem. 1995, 392, 69–74; c) D.
W. Sawyer, J. L. Roberts, J. Electroanal. Chem. 1966, 12, 90-101.
[30] A. A. Frimer, Chem. Rev. 1979, 79, 359-387.
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