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Synfacts 2020; 16(11): 1367
DOI: 10.1055/s-0040-1706528
Peptide Chemistry

Palladium-Catalyzed C(sp3)–H Arylation of Peptides Assisted by Unmodified Asparagine

Contributor(s):
Hisashi Yamamoto
,
Tomohiro Hattori
Weng Y, *, Ding X, Oliveira JC. A, Xu X, Kaplaneris N, Zhu M, Chen H, Chen Z, Ackermann L. * Zhejiang University of Technology, Hangzhou, P. R. of China and Georg-August-Universität Göttingen, Germany
Peptide Late-Stage C(sp3)–H Arylation by Native Asparagine Assistance without Exogenous Directing Group.

Chem. Sci. 2020;
11: 9290-9295
DOI: 10.1039/d0sc.03830j.
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Key words

palladium catalysis - C–H activation - arylation - asparagine

Significance

Late-stage modification of peptides has emerged as an invaluable method in synthetic chemistry. The authors report a C(sp3)–H arylation of peptides by a palladium-catalyzed reaction with internal asparagine (Asn) as a directing group.


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Comment

The site-selective C(sp3)–H arylation proceeded smoothly at the N-termini of di-, tri-, or tetrapeptides, assisted by the unmodified side chain of Asn, without any exogenous directing group.


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Publication History

Article published online:
20 October 2020

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