Synthesis 2020; 52(21): 3253-3262
DOI: 10.1055/s-0040-1707174
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Farzaneh Soleymani Movahed
a  Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
Dinesh N. Sawant
b  Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan   Email: saito.susumu@f.mbox.nagoya-u.ac.jp
,
Dattatraya B. Bagal
a  Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
a  Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
b  Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan   Email: saito.susumu@f.mbox.nagoya-u.ac.jp
› Author Affiliations
This work was supported by a MEXT Grant-in-aid for Scientific Research on Innovative Areas (18H04247 to SS) and a JSPS Scientific Research (B) (19H02713 to SS); and partially funded by Japan Society for the Promotion of Science (JSPS) fellowship for foreign researchers (P18339 to DB).
Further Information

Publication History

Received: 24 April 2020

Accepted after revision: 04 June 2020

Publication Date:
06 July 2020 (online)


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.

Supporting Information

 
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