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Synthesis 2022; 54(16): 3568-3587
DOI: 10.1055/a-1786-6578
DOI: 10.1055/a-1786-6578
feature
On the Copper-Promoted Backbone Arylation of Histidine-Containing Peptides Using Triarylbismuthines
This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), the Centre in Green Chemistry and Catalysis (CGCC), and Boehringer Ingelheim Pharmaceuticals Inc. through a Scientific Advancement Grant.
This paper is dedicated to the memory Dr. Michael Bös for his remarkable contribution to the pharmaceutical industry in the Montreal area and his friendship.
Abstract
We report herein our detailed investigation on the histidine-directed backbone arylation of histidine-containing peptides using triarylbismuth reagents. The reaction proceeds on the backbone NH of the amino acid that precedes the histidine, the so-called n–1 position. The protocol is applicable to dipeptides where the histidine is located at the C-terminus and to tripeptides where the histidine occupies the central position. The transformation is promoted by copper(II) acetate in the presence of phenanthroline (Phen) and diisopropylethylamine in dichloromethane at 50 °C under oxygen. An excellent scope was observed for the triarylbismuthines. In all cases, the imidazole ring of the histidine is protected with a trityl group to prevent the arylation of the side chain. An ATCUN-like model is proposed to explain the observed results.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1786-6578.
- Supporting Information
Publication History
Received: 10 February 2022
Accepted after revision: 02 March 2022
Accepted Manuscript online:
02 March 2022
Article published online:
10 May 2022
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