Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines

Danny C. Lenstra; D. Thao Nguyen; Jasmin Mecinović

doi:10.1016/j.tet.2015.06.066

Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines

Danny C. Lenstra
, D. Thao Nguyen
, Jasmin Mecinović^*

^*Corresponding author for this work

Radboud University Nijmegen

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Development of catalytic amide bond formation reactions from readily available starting materials remains a challenging task for modern organic chemistry. Herein, we report that unactivated carboxylic esters and amines react in the presence of 10 mol % of zirconocene dichloride (Cp₂ZrCl₂) in toluene at 110 °C to afford amides in very good to excellent conversions. The Zr-catalyzed reaction is amenable for the amidation of aliphatic and aromatic carboxylic esters with primary and secondary amines. The reaction proceeds with almost complete retention of configuration for chiral esters and chiral amines.

Original language	English
Journal	Tetrahedron
Volume	71
Issue number	34
Pages (from-to)	5547-5553
ISSN	0040-4020
DOIs	https://doi.org/10.1016/j.tet.2015.06.066
Publication status	Published - 26. Aug 2015
Externally published	Yes

Keywords

Amide bond
Amine
Carboxylic ester
Catalysis
Zirconium

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title = "Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines",

abstract = "Development of catalytic amide bond formation reactions from readily available starting materials remains a challenging task for modern organic chemistry. Herein, we report that unactivated carboxylic esters and amines react in the presence of 10 mol \% of zirconocene dichloride (Cp2ZrCl2) in toluene at 110 °C to afford amides in very good to excellent conversions. The Zr-catalyzed reaction is amenable for the amidation of aliphatic and aromatic carboxylic esters with primary and secondary amines. The reaction proceeds with almost complete retention of configuration for chiral esters and chiral amines.",

keywords = "Amide bond, Amine, Carboxylic ester, Catalysis, Zirconium",

author = "Lenstra, \{Danny C.\} and Nguyen, \{D. Thao\} and Jasmin Mecinovi{\'c}",

year = "2015",

month = aug,

day = "26",

doi = "10.1016/j.tet.2015.06.066",

language = "English",

volume = "71",

pages = "5547--5553",

journal = "Tetrahedron",

issn = "0040-4020",

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TY - JOUR

T1 - Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines

AU - Lenstra, Danny C.

AU - Nguyen, D. Thao

AU - Mecinović, Jasmin

PY - 2015/8/26

Y1 - 2015/8/26

N2 - Development of catalytic amide bond formation reactions from readily available starting materials remains a challenging task for modern organic chemistry. Herein, we report that unactivated carboxylic esters and amines react in the presence of 10 mol % of zirconocene dichloride (Cp2ZrCl2) in toluene at 110 °C to afford amides in very good to excellent conversions. The Zr-catalyzed reaction is amenable for the amidation of aliphatic and aromatic carboxylic esters with primary and secondary amines. The reaction proceeds with almost complete retention of configuration for chiral esters and chiral amines.

AB - Development of catalytic amide bond formation reactions from readily available starting materials remains a challenging task for modern organic chemistry. Herein, we report that unactivated carboxylic esters and amines react in the presence of 10 mol % of zirconocene dichloride (Cp2ZrCl2) in toluene at 110 °C to afford amides in very good to excellent conversions. The Zr-catalyzed reaction is amenable for the amidation of aliphatic and aromatic carboxylic esters with primary and secondary amines. The reaction proceeds with almost complete retention of configuration for chiral esters and chiral amines.

KW - Amide bond

KW - Amine

KW - Carboxylic ester

KW - Catalysis

KW - Zirconium

UR - https://www.scopus.com/pages/publications/84937814615

U2 - 10.1016/j.tet.2015.06.066

DO - 10.1016/j.tet.2015.06.066

M3 - Journal article

AN - SCOPUS:84937814615

SN - 0040-4020

VL - 71

SP - 5547

EP - 5553

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines

Abstract

Keywords

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