C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI

Alkylamino coupling reactions at the C4 positions of 4-halo-1H-1-tritylpyrazoles were investigated using palladium or copper catalysts. The Pd(dba)(2) catalyzed C-N coupling reaction of aryl- or alkylamines, lacking a β-hydrogen atom, proceeded smoothly using (t)BuDavePhos as a ligand. As a substrat...

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Detalles Bibliográficos
Autores principales: Usami, Yoshihide, Tatsui, Yuya, Yoneyama, Hiroki, Harusawa, Shinya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7594063/
https://www.ncbi.nlm.nih.gov/pubmed/33053697
http://dx.doi.org/10.3390/molecules25204634
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author Usami, Yoshihide
Tatsui, Yuya
Yoneyama, Hiroki
Harusawa, Shinya
author_facet Usami, Yoshihide
Tatsui, Yuya
Yoneyama, Hiroki
Harusawa, Shinya
author_sort Usami, Yoshihide
collection PubMed
description Alkylamino coupling reactions at the C4 positions of 4-halo-1H-1-tritylpyrazoles were investigated using palladium or copper catalysts. The Pd(dba)(2) catalyzed C-N coupling reaction of aryl- or alkylamines, lacking a β-hydrogen atom, proceeded smoothly using (t)BuDavePhos as a ligand. As a substrate, 4-Bromo-1-tritylpyrazole was more effective than 4-iodo or chloro-1-tritylpyrazoles. Meanwhile, the CuI mediated C-N coupling reactions of 4-iodo-1H-1-tritylpyrazole were effective for alkylamines possessing a β-hydrogen atom.
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spelling pubmed-75940632020-10-30 C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI Usami, Yoshihide Tatsui, Yuya Yoneyama, Hiroki Harusawa, Shinya Molecules Article Alkylamino coupling reactions at the C4 positions of 4-halo-1H-1-tritylpyrazoles were investigated using palladium or copper catalysts. The Pd(dba)(2) catalyzed C-N coupling reaction of aryl- or alkylamines, lacking a β-hydrogen atom, proceeded smoothly using (t)BuDavePhos as a ligand. As a substrate, 4-Bromo-1-tritylpyrazole was more effective than 4-iodo or chloro-1-tritylpyrazoles. Meanwhile, the CuI mediated C-N coupling reactions of 4-iodo-1H-1-tritylpyrazole were effective for alkylamines possessing a β-hydrogen atom. MDPI 2020-10-12 /pmc/articles/PMC7594063/ /pubmed/33053697 http://dx.doi.org/10.3390/molecules25204634 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Usami, Yoshihide
Tatsui, Yuya
Yoneyama, Hiroki
Harusawa, Shinya
C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI
title C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI
title_full C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI
title_fullStr C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI
title_full_unstemmed C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI
title_short C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)(2) or CuI
title_sort c4-alkylamination of c4-halo-1h-1-tritylpyrazoles using pd(dba)(2) or cui
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7594063/
https://www.ncbi.nlm.nih.gov/pubmed/33053697
http://dx.doi.org/10.3390/molecules25204634
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