Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature.

Dachwitz S, Duwe DH, Hong Wang Y, Gruß H, Hannappel Y, Hellweg T, Sewald N (2020)
Chemistry - A European Journal 26(69): 16357-16364.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Mild reaction conditions are highly desirable for bio-orthogonal side chain derivatizations of amino acids, peptides or proteins due to the sensitivity of these substrates. Transition metal catalyzed cross-couplings such as Suzuki-Miyaura reactions are highly versatile, but usually require unfavourable reaction conditions, in particular, when applied with aryl bromides. Ligand-free solvent-stabilized Pd-nanoparticles represent an efficient and sustainable alternative to conventional phosphine-based catalysts, because the cross-coupling can be performed at considerably lower temperature. We report on the application of such a highly reactive heterogeneous catalyst for the Suzuki-Miyaura cross-coupling of brominated tryptophan derivatives. The solvent-stabilized Pd-nanoparticles are even more efficient than the literature-known ADHP-Pd precatalyst. Interestingly, the latter also leads to the formation of quasi-homogeneous Pd-nanoparticles as the catalytic species. One advantage of our approach is the compatibility with aqueous and aerobic conditions at near-ambient temperatures and short reaction times of only 2 hours. The influence of different N alpha -protecting groups, boronic acids as well as the impact of different amino acid side chains in bromotryptophan-containing peptides has been studied. Notably, a surprising acceleration of the catalysis was observed when palladium-coordinating side chains were present in proximal positions. © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Erscheinungsjahr
2020
Zeitschriftentitel
Chemistry - A European Journal
Band
26
Ausgabe
69
Seite(n)
16357-16364
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2944657

Zitieren

Dachwitz S, Duwe DH, Hong Wang Y, et al. Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature. Chemistry - A European Journal. 2020;26(69):16357-16364.
Dachwitz, S., Duwe, D. H., Hong Wang, Y., Gruß, H., Hannappel, Y., Hellweg, T., & Sewald, N. (2020). Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature. Chemistry - A European Journal, 26(69), 16357-16364. doi:10.1002/chem.202002454
Dachwitz, S., Duwe, D. H., Hong Wang, Y., Gruß, H., Hannappel, Y., Hellweg, T., and Sewald, N. (2020). Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature. Chemistry - A European Journal 26, 16357-16364.
Dachwitz, S., et al., 2020. Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature. Chemistry - A European Journal, 26(69), p 16357-16364.
S. Dachwitz, et al., “Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature.”, Chemistry - A European Journal, vol. 26, 2020, pp. 16357-16364.
Dachwitz, S., Duwe, D.H., Hong Wang, Y., Gruß, H., Hannappel, Y., Hellweg, T., Sewald, N.: Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature. Chemistry - A European Journal. 26, 16357-16364 (2020).
Dachwitz, Steffen, Duwe, Dario H, Hong Wang, Yating, Gruß, Hendrik, Hannappel, Yvonne, Hellweg, Thomas, and Sewald, Norbert. “Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature.”. Chemistry - A European Journal 26.69 (2020): 16357-16364.
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2020-12-22T10:56:12Z
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