Organic Letters
Letter
these results represent an important step toward future studies
in biological systems, which typically consist of various
compartments of either hydrophilic or lipophilic character.
Moreover, our findings can be of value for the initiation of
biphasic polymerizations and other phase transfer related
reactions, especially the hitherto unexploited feature that
unpolar phenyldiazonium iodides apparently possess a low but
sufficient stability to undergo phase transfer.
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ASSOCIATED CONTENT
Supporting Information
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S
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Experimental procedures, characterization data, and
spectra of new compounds (PDF)
4
(
Eur. J. 2011, 17, 4104.
(11) (a) Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317.
AUTHOR INFORMATION
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b) Renaud, P.; Sibi, M. P. Radicals in Organic Synthesis Vol. 1: Basic
Principles; Wiley-VCH: Weinheim, 2001; 1; Chapter 3.1, pp 317−335.
12) For modifications of tyrosine unit in peptides, see: (a) Struck,
Corresponding Author
(
ORCID
A.-W.; Bennett, M. R.; Shepherd, S. A.; Law, B. J. C.; Zhuo, Y.; Wong,
L. S.; Micklefield, J. J. Am. Chem. Soc. 2016, 138, 3038. (b) Bottecchia,
̈
C.; Noel, T. Chem. - Eur. J. 2019, 25, 26.
(13) Sienkiewicz, A.; Losada-Barreiro, S.; Bravo-Díaz, C. J. Phys. Org.
Chem. 2019, 32, 3817.
Present Addresses
‡(
M.C.D.F.) Klocke Pharma Service GmbH, 77767 Appenwe-
ier, Germany.
(
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§
(15) (a) Mo, F.; Dong, G.; Zhang, Y.; Wang, J. Org. Biomol. Chem.
(
G.P.) Landeskriminalamt Baden-Wurttemberg, 70372 Stutt-
̈
2
013, 11, 1582. (b) Trusova, M. E.; Kutonova, K. V.; Kurtukov, V. V.;
Filimonov, V. D.; Postnikov, P. S. Resource-Efficient Technologies 2016,
2, 36.
gart, Germany.
Author Contributions
†L.-M.A. and M.C.D.F. contributed equally.
Notes
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The authors declare no competing financial interest.
(17) (a) Wetzel, A.; Ehrhardt, V.; Heinrich, M. R. Angew. Chem., Int.
Ed. 2008, 47, 9130. (b) Wetzel, A.; Pratsch, G.; Kolb, R.; Heinrich, M.
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ACKNOWLEDGMENTS
We thank Prof. Dr. Franziska Gro
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Einsiedel, J.; Plomer, M.; Hu
Org. Biomol. Chem. 2011, 9, 3746.
18) Hofmann, J.; Clark, T.; Heinrich, M. R. J. Org. Chem. 2016, 81,
̈
bner, H.; Gmeiner, P.; Heinrich, M. R.
̈
hn (FAU) for helpful
discussions. We are also grateful for support by the Deutsche
Forschungsgemeinschaft (DFG) and the Graduate School
Molecular Science (GSMS) (L.-M.A.). The financial support
by the Studienstiftung des Deutschen Volkes (M.C.D.F.) is
also gratefully acknowledged.
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