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Diphenylsilane as a coupling reagent for amide bond formation

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Abstract

A simple procedure for amide bond formation using diphenylsilane as a coupling reagent is described. This methodology enables the direct coupling of carboxylic acids with primary and secondary amines, releasing only hydrogen and a siloxane as by-products. Only one equivalent of each partner is needed, providing a more sustainable amidation method producing minimal wastes. This methodology was also extended to the synthesis of peptides and lactams by addition of Hünig's base (DIPEA) and 4-dimethylaminopyridine (DMAP).

Graphical abstract: Diphenylsilane as a coupling reagent for amide bond formation

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Publication details

The article was received on 29 Aug 2017, accepted on 29 Sep 2017 and first published on 29 Sep 2017


Article type: Communication
DOI: 10.1039/C7GC02643A
Citation: Green Chem., 2017, Advance Article
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    Diphenylsilane as a coupling reagent for amide bond formation

    M. Sayes and A. B. Charette, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC02643A

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