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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...

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Autores principales: Zhang, Peng, Cook, Andrea M., Liu, Yang, Wolf, Christian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
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.
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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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