Chemistry - A European Journal
10.1002/chem.201805737
COMMUNICATION
[
10] a) N. Y. More, M. Jeganmohan, Chem. Commun. 2017, 53, 9616–9619;
b) Z. Maeno, T. Mitsudome, T. Mizugaki, K. Jitsukawa, Catal. Sci.
Technol. 2017, 7, 3205–3209; c) K. Morimoto, K. Sakamoto, Y. Ohnishi,
T. Miyamoto, M. Ito, T. Dohi, Y. Kita, Chem. Eur. J. 2013, 19, 8726–
Acknowledgements
S.R.W. appreciates the financial support by the DFG
8731.
(
Wa1276/14-1). R.B. thanks the Austrian Science Fund (FWF)
[11] a) K. Morimoto, K. Sakamoto, T. Ohshika, T. Dohi, Y. Kita, Angew.
Chem. Int. Ed. 2016, 55, 3652–3656; Angew. Chem. 2016, 128, 3716–
for financial support (Project I-2712).
3
720; b)
12] H. Shalit, A. Libman, D. Pappo, J. Am. Chem. Soc. 2017, 139, 13404–
3413.
[
1
Keywords: C-H activation, cross-coupling, dehydrogenation,
[
[
13] D. Wahl, Galvanotechnik 2005, 96, 1600–1610.
14] a) B. Elsler, D. Schollmeyer, K. M. Dyballa, R. Franke, S. R. Waldvogel,
Angew. Chem. Int. Ed. 2014, 53, 5210–5213; Angew. Chem. 2014, 126,
electrochemistry, anode
5
311–5314 b) S. Lips, A. Wiebe, B. Elsler, D. Schollmeyer, K. M.
Dyballa, R. Franke, S. R. Waldvogel, Angew. Chem. Int. Ed. 2016, 55,
0872–10876; Angew. Chem. 2016, 128, 11031–11035 c) A. Wiebe, D.
[
1]
A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722–6737;
Angew. Chem. 2011, 123, 6854–6869; b) E.-i. Negishi, Angew.
Chem. Int. Ed. 2011, 50, 6738–6764; Angew. Chem. 2011, 123,
1
Schollmeyer, K. M. Dyballa, R. Franke, S. R. Waldvogel, Angew. Chem.
Int. Ed. 2016, 55, 11801–11805; Angew. Chem. 2016, 128, 11979–
6870–6897; c) M. Grzybowski, K. Skonieczny, H. Butenschön, D. T.
Gryko, Angewandte Chemie Int. Ed. 2013, 52, 9900–9930; Angew.
Chem. 2013, 125, 10084–10115.
a) I. Hussain, T. Singh, Adv. Synth. Catal. 2014, 356, 1661–1696. b) G.
Bringmann, A. J. Price Mortimer, P. A. Keller, M. J. Gresser, J. Garner,
M. Breuning, Angew. Chem. Int. Ed. 2005, 44, 5384–5427; Angew.
Chem. 2005, 117, 5518–5563;
11983; d) A. Wiebe, B. Riehl, S. Lips, R. Franke, S. R. Waldvogel, Sci.
Adv. 2017, 3, eaao3920/1–7; e) A. Kirste, B. Elsler, G. Schnakenburg,
S. R. Waldvogel, J. Am. Chem. Soc. 2012, 134, 3571–3576; f) A. Kirste,
G. Schnakenburg, F. Stecker, A. Fischer, S. R. Waldvogel, Angew.
Chem. Int. Ed. 2010, 49, 971–975; Angew. Chem. 2010, 122, 983–987;
g) L. Schulz, M. Enders, B. Elsler, D. Schollmeyer, K. M. Dyballa, R.
Franke, S. R. Waldvogel, Angew. Chem. Int. Ed. 2017, 56, 4877–4881;
Angew. Chem. 2017, 129, 4955–4959; h) A. Wiebe, S. Lips, D.
[
2]
3]
[
a) F. v. Nussbaum, M. Brands, B. Hinzen, S. Weigand, D. Häbich,
Angew. Chem. Int. Ed. 2006, 45, 5072–5129; Angew. Chem. 2006, 118,
5
194–5254; b) J. Schimana, K. Gebhardt, A. Höltzel, D. G. Schmid, R.
Süssmuth, J. Müller, R. Pukall, H.-P. Fiedler, J. Antibiot. 2002, 55, 565–
70; c) A. F. P. Biajoli, C. S. Schwalm, J. Limberger, T. S. Claudino, A.
Schollmeyer, R. Franke, S. R. Waldvogel, Angew. Chem. Int. Ed. 2017,
56, 14727–14731; Angew. Chem. 2017, 129, 14920–14925, i) A. Kirste,
5
G. Schnakenburg, S. R. Waldvogel, Org. Lett. 2011, 13, 3126–3129.
15] a) A. Wiebe, T. Gieshoff, S. Möhle, E. Rodrigo, M. Zirbes, S. R.
Waldvogel, Angew. Chem. Int. Ed. 2018, 57, 5594–5619; Angew.
Chem. 2018, 130, 5694–5721; b) S. Möhle, M. Zirbes, E. Rodrigo, T.
Gieshoff, A. Wiebe, S. R. Waldvogel, Angew. Chem. Int. Ed. 2018; 57,
L. Monteiro, J. Braz. Chem. Soc. 2014, 25, 2186–2214; d) J. Magano, J.
R. Dunetz, Chem. Rev. 2011, 111, 2177–2250.
[
[4]
a) K. Okamoto, J. Zhang, J. B. Housekeeper, S. R. Marder, C. K.
Luscombe, Macromolecules 2013, 46, 8059–8078; b) M. Hoyos, M. L.
Turner, O. Navarro, Curr. Org, Chem. 2011, 15, 3263–3290; c) C.
Böttcher, G. Zeyat, S. A. Ahmed, E. Irran, T. Cordes, C. Elsner, W.
Zinth, K. Rueck-Braun, Beilstein J. Org. Chem. 2009, 5, No. 25; d) E.-i.
Negishi (Ed.) Handbook of Organopalladium Chemistry for Organic
Synthesis, John Wiley & Sons, Inc, New York, USA, 2002.
6018–6041; Angew. Chem. 2018, 130, 6124–6149; c) B. A. Frontana-
Uribe, R. D. Little, J. G. Ibanez, A. Palma, R. Vasquez-Medrano, Green
Chem. 2010, 12, 2099–2119; d) M. Yan, Y. Kawamata, P. S. Baran,
Chem. Rev. 2017, 117, 13230–13319, e) E. J. Horn, B. R. Rosen, P. S.
Baran, ACS Cent. Sci. 2016, 2, 302–308; f) H. J. Schäfer, Angew.
Chem. Int. Ed. 2017, 56, 15502–15503; Angew. Chem. 2017, 129,
[
5]
6]
a) G. Bringmann, T. Gulder, T. A. M. Gulder, M. Breuning, Chem. Rev.
2011, 111, 563–639; b) J.-S. Chen, Y.-L. Chen, A. S. Greenberg, Y.-J.
15706–15708.
Chen, S.-M. Wang, J. Cell. Biochem. 2005, 94, 1028–1037.
a) A. Boudier, P.-A. R. Breuil, L. Magna, H. Olivier-Bourbigou, P.
Braunstein, Dalton Trans. 2015, 44, 12995–12998; b) A. Vidal-Ferran, I.
Mon, A. Bauzá, A. Frontera, L. Rovira, Chem. – Eur. J. 2015, 21,
[
[
16] a) M. Quan, D. Sanchez, M. F. Wasylkiw, D. K. Smith, J. Am. Chem.
Soc. 2007, 129, 12847–12856; b) G. Wang, C. Feng, Polymers 2017, 9,
[
220.
17] a) B. Elsler, A. Wiebe, D. Schollmeyer, K. M. Dyballa, R. Franke, S. R.
Waldvogel, Chem. - Eur. J. 2015, 21, 12321–12325; b) I. Colomer, A. E.
R. Chamberlain, M. B. Haughey, T. J. Donohoe, Nat. Rev. Chem. 2017,
11417–11426; c) Y.-J. Liu, Z.-Z. Zhang, S.-Y. Yan, Y.-H. Liu, B.-F. Shi,
Chem. Commun. 2015, 51, 7899–7902; d) R. Franke, D. Selent, A.
Börner, Chem. Rev. 2012, 112, 5675–5732; d) J. B. Alexander, D. S.
La, D. R. Cefalo, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc.
1
(88), 1–12.
[18] a) C. Gütz, B. Klöckner, S. R. Waldvogel, Org. Process Res. Dev. 2016,
0, 26–32;
1998, 120, 4041–4042; e) A. F. Kiely, J. A. Jernelius, R. R. Schrock, A.
2
H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 2868–2869.
[
19] a) A. Kirste, B. Elsler, G. Schnakenburg, S. R. Waldvogel, J. Am. Chem.
Soc. 2012, 134, 3571–3576; b) A. Kirste, G. Schnakenburg, F. Stecker,
A. Fischer, S. R. Waldvogel, Angew. Chem. Int. Ed. 2010, 49, 971–975;
Angew. Chem. 2010, 122, 983–987.
20] J. K. Badenhoop, F. Weinhold, J. Chem. Phys. 1997, 107, 5422–5432.
21] a) S. R. Waldvogel, D. Mirks, Tetrahedron Lett. 2000, 41, 4769–4772; b)
M. C. Schopohl, A. Faust, D. Mirk, R. Fröhlich, O. Kataeva, S. R
Waldvogel, Eur. J. Org. Chem. 2005, 2987–2999; c) 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.
[
7]
8]
a) M. Sentürk, I. Gülçin, A. Daştan, O. I. Küfrevioğlu, C. T. Supuran,
Bioorg. Med. Chem. 2009, 17, 3207–3211; b) B. J. Wu, K. Kathir, P. K.
Witting, K. Beck, K. Choy, C. Li, K. D. Croft, T. A. Mori, D. Tanous, M.
R. Adams et al., J. Exp. Med. 2006, 203, 1117–1127; c) I. Güllçin, A.
Daştan, J. Enzyme Inhib. Med. Chem. 2007, 22, 685–695.
a) M. Trobe, R. Breinbauer, Monatsh. Chem. 2016, 147, 509–521; b) M.
Peters, M. Trobe, H. Tan, R. Kleinweischede, R. Breinbauer, Chem.
Eur. J. 2013, 19, 2442–2449; c) M. Peters, M. Trobe, R. Breinbauer,
Chem. Eur. J. 2013, 19, 2450–2456; d) M. Trobe, M. Peters, S. H.
Grimm, R. Breinbauer, Synlett 2014, 25, 1202–1214; e) B. P. Orner, J.
T. Ernst, A. D. Hamilton, J. Am. Chem. Soc. 2001, 123, 5382–5383.; f) I.
Saraogi, A. D. Hamilton, Biochem. Soc. Trans. 2008, 36, 1414–1417.
C. G. Cummings, A. D. Hamilton, Curr. Opin. Chem. Biol. 2010, 14,
[
[
[
2006, 241–245; d) C. Regenbrecht, S. R. Waldvogel, Beilstein J. Org.
Chem. 2012, 1721–1724; e) S. R. Waldvogel, S. Lips, M. Selt, B. Riehl,
C. J. Kampf, Chem. Rev. 2018, 118, 6706–6765. .
[9]
341–346.
This article is protected by copyright. All rights reserved.