10.1002/ejoc.202001003
European Journal of Organic Chemistry
COMMUNICATION
bathochromically shifted band triggered the photoreaction, which
resulted in synthetically valuable C-H functionalizations.
Alkylated products were isolated in good to high yields for
substrates such as trimethylsilyl ethers and derivatives of pyrrole,
furan, thiophene and indole, and further expansion of the
methodology to more complex products are underway.
[10] B. Schweitzer-Chaput, M. A. Horwitz, E. de Pedro Beato, P.
Melchiorre, Nat. Chem. 2019, 11, 129-135.
[11] D. Spinnato, B. Schweitzer-Chaput, G. Goti. M. Ošeka, P.
Melchiorre, Angew. Chem. Int. Ed. 2020, 59, 2-8; Angew.
Chem. 2020,132, 2-8.
[12] M. Tobisu, T. Furukawa, N. Chatani, Chem. Lett. 2013, 42,
1203-1205.
[13] S. R. Kandukuri, A. Bahamonde, I. Chatterjee, I.
D. Jurberg, E. C. Escudero-Adán, P. Melchiorre, Angew.
Chem. Int. Ed. 2015, 54, 1485-1489; Angew. Chem. 2015,
127, 1505-1509.
[14] X. Sun, W. Wang, Y. Li, J. Ma, S. Yu, Org. Lett. 2016, 18,
4638-4641.
[15] Further selected examples: a) E. Arceo, I. D. Jurberg, A.
Álvarez‐Fernández, P. Melchiorre, Nat. Chem. 2013, 5,
750; b) M. Nappi, G. Bergonzini, P. Melchiorre, Angew.
Chem. Int. Ed. 2014, 53, 4921-4925; c) Ł. Woźniak, J. J.
Murphy, P. Melchiorre, J. Am. Chem. Soc. 2015, 137, 17,
5678-5681;
Acknowledgements
We acknowledge financial support from the Ludwig-
Maximilians-University Munich, the Max-Planck-Society
(Max-Planck-Fellow Research Group Origins of Life), the
Deutsche Forschungsgemeinschaft DFG (INST 86/1807-1
FUGG) and the Volkswagen Stiftung (Initiating Molecular
Life). We thank Dr. Peter Mayer for the X-ray structure
analysis.
d) H.-H. Zhang, S. Yu, Org. Lett. 2019, 21, 3711– 3715;
e) S. Xie, D. Li, H. Huang, F. Zhang, Y. Chen, J. Am.
Chem. Soc. 2019, 141, 16237– 16242; f) J. Wu, P. S.
Grant, X. Li, A. Noble, V. K. Aggarwal, Angew. Chem. Int.
Ed. 2019, 58, 5697– 5701.
Conflict of interest
[16] J. Wu, P. S. Grant,X. Li, A. Noble, V. K. Aggarwal, Angew.
Chem. Int. Ed. 2019, 58, 5697– 5701.
The authors declare no conflict of interest.
[17] a) F. Sandfort, F. Strieth-Kalthoff, F. J. R. Klauck, M.
J.James, F. Glorius, Chem. - Eur. J. 2018, 24, 17210–
17214; b) M. J. James, F. Strieth-Kalthoff, F. Sandfort, F. J.
R. Klauck, F. Wagener, F. Glorius, Chem. - Eur. J. 2019,
25, 8240– 8244
Keywords: alkylation • C-H functionalization • photochemistry •
radicals • synthetic methods
[18] M.-C. Fu, R. Shang, B. Zhao, B. Wang, Y. Fu, Science
2019, 363, 1429– 1434.
[19] G. E. M. Crisenza, D. Mazzarella, P. Melchiorre, J. Am.
Chem. Soc. 2020, 142, 5461-5476.
[20] A. C. Closs, E. Fuks, M. Bechtel, O. Trapp, Chem. Eur. J.,
10.1002/chem.202001514
[1] a) G. Ciamician, Science 1912, 36, 385–394; for reviews
on photochemistry see: b) J. M. R. Narayanam, C. R. J.
Stephenson, Chem. Soc. Rev. 2011, 40, 102–113; c) N.
Hoffmann, Chem. Rev. 2008, 108, 1052–1103; d) M.
Fagnoni, D. Dondi, D. Ravelli and A. Albini, Chem. Rev.
2007, 107, 2725–2756.
[2] T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton,
D. W. C. MacMillan, Science 2007, 316, 582-585.
[3] D. W. C. MacMillan, Nature 2008, 455, 304–308.
[4] M. A. Ischay, M. E. Anzovino, J. Du, T. P. Yoon, J. Am.
Chem. Soc. 2008, 130, 12886-12887.
[5] J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, J.
Am. Chem. Soc. 2009, 131, 8756-8757.
[6] N. A. Romero, D. A. Nicewicz, Chem. Rev. 2016, 116,
10075-10166.
[7] a) C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem.
Rev. 2013, 113, 5322–5363; b) F. Teplý, Collect. Czech.
Chem. Commun. 2011, 76, 859-917.
[8] a) A. G. Condie, J. C. González‐Gómez, C. R. J.
Stephenson, J. Am. Chem. Soc. 2010, 132, 1464-1465;
b) D. Staveness, I. Bosque, C.R. J. Stephenson Acc.
Chem. Res. 2016, 49, 2295−2306; c) C. J. O´Brien, D. G.
Droege, A. Y. Jui, S. S. Gandhi, N. A. Paras, S. H. Olson,
J. Conrad, J. Org. Chem. 2018, 83, 8926−8935.
[21] a) S. Lakhdar, B. Maji, H. Mayr, Angew. Chem. Int. Ed.
2012, 51, 5739–5742; b) H. Mayr, T. Bug, M. F. Gotta, N.
Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R.
Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc.
2001, 123, 9500-9512.
[22] C. G. S. Lima, T. de M. Lima, M. Duarte, I. D. Jurberg, M.
W. Paixão, ACS Catal. 2016, 6, 1389-1407.
[23] U. Megerle, R. Lechner, B. König, E. Riedle, Photochem.
Photobiol. Sci. 2010, 9, 1400-1406.
[24] A. Gerwien, P. Mayer, H. Dube, Nat. Commun. 2019, 10,
4449.
[25] J. Tucher, S. Schlicht, F. Kollhoff, C. Streb, Dalton Trans.
2014, 43, 17029-17033.
Int. Ed. 2019, 58, 3730 – 3747
[27] M. Cismesia, T. P Yoon, Chem. Sci. 2015, 6, 5426-5434
[ 28 ] S.R. Waldvogel in Fundamentals and Applications of
Organic Electrochemistry. Synthesis, Materials, Devices.
By T. Fuchigami, M. Atobe, S. Inagi, Wiely & Sons, Ltd.
2015.
[29] a) M. K. Mishra, S. Lenka, P. L. Nayak, J. Polym. Sci. Pol.
Toniolo Tetrahedron Lett.2001, 42, 6279-6282.
[30] S. L. Rössler, B. J. Jelier, E. Magnier, G. Dagousset, E. M.
Carreira, A. Togni, Angew. Chem. Int. Ed. 2020, 59, 9264-
9280.
[9] a) M. Neumann, S. Füldner, B. König, K. Zeitler, Angew.
Chem. 2011, 123, 981-985; Angew. Chem. Int. Ed. 2011,
50, 951–954; b) K. Zeitler, Angew. Chem. 2009, 121,
9969–9974; Angew. Chem. Int. Ed. 2009, 48, 9785–9789;
c) I. Ghosh, T. Ghosh, J. I. Bardagi, B. König, Science
2014, 346, 725-728; d) C. Bottecchia, R. Martín, I. Abdaij,
E. Crovini, J. Alcazar, J. Orduna, M. J. Blesa, J. R. Carrillo,
P. Prieto, T. Noël, Adv. Synth. Catal. 2019, 361, 945 –950.
[31] Z.-J. Li,
S. Li, E. Hofman, A. H. Davis, G. Leem, W.
Zheng, Green Chem. 2020, 22, 1911-1918.
[32] R. J. Sundberg in Heterocyclic Scaffolds II: Reactions and
Applications of Indoles, Vol. 26 (Ed.: B.U. W. Maes),
Springer-Verlag Berlin Heidelberg, 2011, p. 47-115.
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