Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds Between Aromatic Acids and Amines

Farzaneh Soleymani Movahed; Dinesh N. Sawant; Dattatraya B. Bagal; Susumu Saito

doi:10.1055/s-0040-1707174

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(21): 3253-3262
DOI: 10.1055/s-0040-1707174

special topic

Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds Between Aromatic Acids and Amines

Farzaneh Soleymani Movahed

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

,

Dinesh N. Sawant

^bResearch Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan eMail: saito.susumu@f.mbox.nagoya-u.ac.jp

,

Dattatraya B. Bagal

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

,

Susumu Saito ∗

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

^bResearch Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan eMail: saito.susumu@f.mbox.nagoya-u.ac.jp

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Abstract

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Published as part of the Special Topic Recent Advances in Amide Bond Formation

Abstract

The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using ³¹P NMR spectroscopy and ESI mass spectrometry.

Key words

amide bond formation - organophosphorus catalyst - dehydration - carboxylic acids - amines

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