Room temperature N-arylation of amino acids and peptides using copper(I) and β-diketone

Organic & Biomolecular Chemistry
Krishna K SharmaRahul Jain

Abstract

A mild and efficient method for the N-arylation of zwitterionic amino acids, amino acid esters and peptides is described. The procedure provides the first room temperature synthesis of N-arylated amino acids and peptides using CuI as a catalyst, diketone as a ligand, and aryl iodides as coupling partners. The method is equally applicable for using relatively inexpensive aryl bromides as coupling partners at 80 °C. Using this procedure, electronically and sterically diverse aryl halides, containing reactive functional groups were efficiently coupled in good to excellent yields.

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Citations

Aug 9, 2016·Organic Letters·Sandra M King, Stephen L Buchwald
Aug 24, 2016·Chemistry : a European Journal·Sepideh SharifMichael G Organ
Oct 8, 2016·Organic & Biomolecular Chemistry·Krishna K SharmaRahul Jain
Jan 23, 2021·Chemistry : a European Journal·Gabriella KerveforsBerit Olofsson
Mar 25, 2019·Journal of the American Chemical Society·Yu KawamataPhil S Baran
Dec 4, 2019·The Journal of Organic Chemistry·Hailey A YoungCaroline Proulx

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