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Copper(I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated N-Heterocycles
[Image: see text] The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon–carbon bond formation provides convenient access to a variety of...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4017613/ https://www.ncbi.nlm.nih.gov/pubmed/24724797 http://dx.doi.org/10.1021/jo500365h |
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author | Zhang, Peng Cook, Andrea M. Liu, Yang Wolf, Christian |
author_facet | Zhang, Peng Cook, Andrea M. Liu, Yang Wolf, Christian |
author_sort | Zhang, Peng |
collection | PubMed |
description | [Image: see text] The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon–carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing the corresponding 1,2-dihydro-N-heterocycles in up to 95% yield. |
format | Online Article Text |
id | pubmed-4017613 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-40176132015-04-11 Copper(I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated N-Heterocycles Zhang, Peng Cook, Andrea M. Liu, Yang Wolf, Christian J Org Chem [Image: see text] The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon–carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing the corresponding 1,2-dihydro-N-heterocycles in up to 95% yield. American Chemical Society 2014-04-11 2014-05-02 /pmc/articles/PMC4017613/ /pubmed/24724797 http://dx.doi.org/10.1021/jo500365h Text en Copyright © 2014 American Chemical Society |
spellingShingle | Zhang, Peng Cook, Andrea M. Liu, Yang Wolf, Christian Copper(I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated N-Heterocycles |
title | Copper(I)-Catalyzed Nucleophilic
Addition of Ynamides
to Acyl Chlorides and Activated N-Heterocycles |
title_full | Copper(I)-Catalyzed Nucleophilic
Addition of Ynamides
to Acyl Chlorides and Activated N-Heterocycles |
title_fullStr | Copper(I)-Catalyzed Nucleophilic
Addition of Ynamides
to Acyl Chlorides and Activated N-Heterocycles |
title_full_unstemmed | Copper(I)-Catalyzed Nucleophilic
Addition of Ynamides
to Acyl Chlorides and Activated N-Heterocycles |
title_short | Copper(I)-Catalyzed Nucleophilic
Addition of Ynamides
to Acyl Chlorides and Activated N-Heterocycles |
title_sort | copper(i)-catalyzed nucleophilic
addition of ynamides
to acyl chlorides and activated n-heterocycles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4017613/ https://www.ncbi.nlm.nih.gov/pubmed/24724797 http://dx.doi.org/10.1021/jo500365h |
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