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

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

*Kontaktforfatter for dette arbejde

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

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.

OriginalsprogEngelsk
TidsskriftTetrahedron
Vol/bind71
Udgave nummer34
Sider (fra-til)5547-5553
ISSN0040-4020
DOI
StatusUdgivet - 26. aug. 2015
Udgivet eksterntJa

Fingeraftryk

Amides
Amines
Esters
Organic Chemistry
Toluene
Zirconocene dichloride

Citer dette

Lenstra, Danny C. ; Nguyen, D. Thao ; Mecinović, Jasmin. / Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines. I: Tetrahedron. 2015 ; Bind 71, Nr. 34. s. 5547-5553.
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Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines. / Lenstra, Danny C.; Nguyen, D. Thao; Mecinović, Jasmin.

I: Tetrahedron, Bind 71, Nr. 34, 26.08.2015, s. 5547-5553.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

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

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DO - 10.1016/j.tet.2015.06.066

M3 - Journal article

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JO - Tetrahedron

JF - Tetrahedron

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