Communication
ChemComm
that the photoreaction is initiated by a single electron transfer 12 H. Braunschweig, M. A. Celik, T. Dellermann, G. Frenking, K. Hammond,
F. Hupp, H. Kelch, I. Krummenacher, F. Lindl, L. Mailaender, J. H.
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from 2 to the halogen containing solvent. The reaction is not
limited to aminoboroles, but also proceeds upon irradiation
of N,N-bis(trimethylsilyl)aniline 10. The limited data that is
currently available suggests that an ionization potential of around
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3 S. Yruegas, J. J. Martinez and C. D. Martin, Chem. Commun., 2018,
54, 6808.
4 F. Lindl, S. Lin, I. Krummenacher, C. Lenczyk, A. Stoy, M. Mueller,
Z. Lin and H. Braunschweig, Angew. Chem., Int. Ed., 2019, 58, 338.
5 W. Zhang, G. Li, L. Xu, Y. Zhuo, W. Wan, N. Yan and G. He, Chem.
Sci., 2018, 9, 4444.
6 M. M u¨ ller, C. Maichle-M ¨o ssmer and H. F. Bettinger, Angew. Chem.,
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7 H. F. Bettinger and M. M u¨ ller, J. Phys. Org. Chem., 2015, 28, 97.
6
eV is required for a substrate to undergo the SET mechanism.
The target compound 9-amino-9-borafluorene is unstable under
photoirradiation and undergoes cyclooligomerization, most
likely to the dimer.
C. K. thanks the Fonds der chemischen Industrie for a 18 L. K. Madden, A. M. Mebel, M. C. Lin and C. F. Melius, J. Phys. Org.
Chem., 1996, 9, 801.
9 H. F. Bettinger, P. R. Schreiner, H. F. Schaefer and P. v. R. Schleyer,
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Fellowship. The work was supported in part by the Deutsche
Forschungsgemeinschaft (DFG). The computations were per-
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formed on the BwForCluster JUSTUS. The authors acknowledge 20 L. T. Scott, N. H. Roelofs and T.-H. Tsang, J. Am. Chem. Soc., 1987,
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09, 5456.
support by the state of Baden-W u¨ rttemberg through bwHPC
and the DFG through grant no INST 40/467-1 FUGG. We thank
Prof. Todd Marder for the LIFDI measurement.
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Conflicts of interest
25 J. Radtke, S. K. Mellerup, M. Bolte, H.-W. Lerner, S. Wang and
M. Wagner, Org. Lett., 2018, 20, 3966.
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6 K. Ansorg, H. Braunschweig, C.-W. Chiu, B. Engels, D. Gamon, M. Huegel,
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There are no conflicts to declare.
27 V. A. K. Adiraju and C. D. Martin, Chem. – Eur. J., 2017, 23, 11437.
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